Advertisement

Story of Eribulin Mesylate: Development of the Longest Drug Synthesis

Chapter
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 44)

Abstract

Eribulin mesylate (Halaven™), approved in 2010 as an anticancer agent, represents a simplified analogue of the marine natural product halichondrin B, which was isolated in 1986 from the sea sponge Halichondria okadai. The story of the discovery, development, and launch of this drug impressively demonstrates how far the limits of total synthesis of natural products have been pushed today on an industrial scale since it can be considered the most complex synthetic drug today.

Keywords

Anticancer drugs Breast cancer Catalytic asymmetric Nozaki–Hiyama–Kishi reaction Eribulin Fragment coupling Halaven Halichondria okadai Halichondrin Homohalichondrin Macrolide Marine natural products Norhalichondrin Nozaki–Hiyama–Kishi reaction Polyether Process development Scale-up Structure-activity relationships Total synthesis Transition-metal-mediated coupling reactions 

Abbreviations

(DHQ)2AQN

Hydroquinine anthraquinone-1,4-diyl diether

(DHQ)2PYR

Hydroquinine 2,5-diphenyl-4,6-pyrimidinediyl diether

9-BBN

9-Borabicyclo[3.3.1]nonane

Ac

Acetyl

AD

Asymmetric dihydroxylation

API

Active pharmaceutical ingredient

aq

Aqueous

Ar

Aryl

asymm.

Asymmetric

BHT

Butylated hydroxytoluene, 2,6-di-tert-butyl-4-methylphenol

B-I-9-BBN

B-iodo-9-borabicyclo[3.3.1]nonane

BINOL

1,1′-Bi-2-naphthol

Bn

Benzyl

Boc

tert-Butoxycarbonyl

Bz

Benzoyl

cat.

Catalyst, catalytic

CoPc

Cobalt phthalocyanine

Cp

Cyclopentadienyl

CSA

Camphorsulfonic acid

Cy

Cyclohexyl

DBU

1,8-Diazabicyclo[5.4.0]undec-7-ene

DDQ

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

de

Diastereomer excess

DEAD

Diethyl azodicarboxylate

DEP

2,9-Diethyl-1,10-phenanthroline

DIAD

Diisopropyl azodicarboxylate

DIBAL-H

Diisobutylaluminum hydride

DIEA

N,N-Diisopropylethylamine

DLD-1

Human colorectal adenocarcinoma cancer cell line isolated by D. L. Dexter

DMAP

4-(Dimethylamino)pyridine

DMDO

Dimethyldioxirane

DME

1,2-Dimethoxyethane

DMF

Dimethylformamide

DMP

2,9-Dimethyl-1,10-phenanthroline

DMPU

1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

DMSO

Dimethyl sulfoxide

dr

Diastereomer ratio

DTBMP

2,6-Di-tert-butyl-4-methylpyridine

ee

Enantiomeric excess

equiv.

Equivalent(s)

Et

Ethyl

EtCN

Propionitrile

g

Gram

GMP

Good manufacturing practice

HWE

Horner–Wadsworth–Emmons (reaction)

Light

im

Imidazole

i-Pr

Isopropyl

kg

Kilogram

KHMDS

Potassium hexamethyldisilazide, potassium bis(trimethylsilyl)amide

LAH

Lithium aluminum hydride

LDA

Lithium diisopropylamide

LiHMDS

Lithium hexamethyldisilazide, lithium bis(trimethylsilyl)amide

LOX

Metastatic human melanoma cell line

MDR

Multidrug resistant

Me

Methyl

Me2CO

Acetone

MeCN

Acetonitrile

Mes

Mesityl, 2,4,6-trimethylphenyl (not methanesulfonyl)

mL

Milliliter

MMTr

Monomethoxy trityl

MNBA

2-Methyl-6-nitrobenzoic anhydride (Shiina’s reagent)

mol

Mole(s)

MOM

Methoxymethyl

Ms

Methanesulfonyl (mesyl)

MTBE

Methyl tert-butyl ether

NaHMDS

Sodium hexamethyldisilazide, sodium bis(trimethylsilyl)amide

n-Bu

n-Butyl

NCI

United States National Cancer Institute

NCS

N-Chlorosuccinimide

ng

Nanogram

NHK

Nozaki–Hiyama–Kishi (reaction)

NiCl2·DEP

Nickel(II)-chloride 2,9-diethyl-1,10-phenanthroline complex

NiCl2·DMP

Nickel(II)-chloride 2,9-dimethyl-1,10-phenanthroline complex

NIS

N-Iodosuccinimide

NMM

N-Methylmorpholine

NMO

N-Methylmorpholine N-oxide

NMP

N-Methyl-2-pyrrolidone

P-gp

P-Glycoprotein

Ph

Phenyl

PhH

Benzene

PhMe

Toluene

PMB

4-Methoxybenzyl

PMP

4-Methoxyphenyl

PNB

4-Nitrobenzoyl

PNBCl

4-Nitrobenzoyl chloride

PNBOH

4-Nitrobenzoic acid

PPTS

Pyridinium p-toluenesulfonate

p-TsOH

4-Toluenesulfonic acid

Pv

Pivaloyl

py

Pyridine

Raney Ni

Raney nickel

RCM

Ring-closing metathesis

rt

Room temperature

SAR

Structure-activity relationship(s)

Sia

1,2-Dimethylpropyl

SMB

Simulated moving bed

SN

Nucleophilic substitution

TBAF

Tetra-n-butylammonium fluoride

TBDPS

tert-Butyldiphenylsilyl

TBS

tert-Butyldimethylsilyl

t-Bu

tert-Butyl

TEMPO

(2,2,6,6-Tetramethylpiperidin-1-yl)oxyl

TES

Triethylsilyl

Tf

Trifluoromethanesulfonyl (triflyl)

TFA

Trifluoroacetic acid

THF

Tetrahydrofuran

TMEDA

N,N,N′,N′-Tetramethyl-1,2-ethylenediamine

TMS

Trimethylsilyl

TPAP

Tetra-n-propylammonium perruthenate

Ts

Tosyl, 4-toluenesulfonyl

References

  1. 1.
    Uemura D, Takahashi K, Yamamoto T (1985) J Am Chem Soc 107:4796–4798CrossRefGoogle Scholar
  2. 2.
    Tachibana K, Scheuer PJ, Tsukitani Y, Kikuchi H, Van Engen D, Clardy J, Gopichand Y, Schmitz FJ (1981) J Am Chem Soc 103:2469–2471CrossRefGoogle Scholar
  3. 3.
    Hirata Y, Uemura D (1986) Pure Appl Chem 58:701–710CrossRefGoogle Scholar
  4. 4.
    Yamamoto A, Ueda A, Brémond P, Tiseni PS, Kishi Y (2012) J Am Chem Soc 134:893–896CrossRefGoogle Scholar
  5. 5.
    Pettit GR, Tan R, Gao F, Williams MD, Doubek DL, Boyd MR, Schmidt JM, Chapuis J-C, Hamel E, Bai R, Hooper JNA, Tackett LP (1993) J Org Chem 58:2538–2543CrossRefGoogle Scholar
  6. 6.
    Litaudon M, Hart JB, Blunt JW, Lake RJ, Munro MHG (1994) Tetrahedron Lett 35:9435–9438CrossRefGoogle Scholar
  7. 7.
    Litaudon M, Hickford SJH, Lill RE, Lake RJ, Blunt JW, Munro MHG (1997) J Org Chem 62:1868–1871CrossRefGoogle Scholar
  8. 8.
    Hickford SJH, Blunt JW, Munro MHG (2009) Bioorg Med Chem 17:2199–2203CrossRefGoogle Scholar
  9. 9.
    Pettit GR, Herald CL, Boyd MR, Leed JE, Dufresne C, Doubek DL, Schmidt JM, Cerny RL, Hooper JNA, Rützler KC (1991) J Med Chem 34:3339–3340CrossRefGoogle Scholar
  10. 10.
    Jackson KL, Henderson JA, Philips AJ (2009) Chem Rev 209:3044–3079CrossRefGoogle Scholar
  11. 11.
    Bai R, Paull KD, Heraldy CL, Malspeis L, Pettit GR, Hamel E (1991) J Biol Chem 266:15882–15889Google Scholar
  12. 12.
    Ludueña RF, Roach MC, Prasad V, Pettit GR (1993) Biochem Pharmacol 45:421–427CrossRefGoogle Scholar
  13. 13.
    Dabydeen D, Burnett JC, Bai R, Verdier-Pinard P, Hickford SJH, Pettit GR, Blunt JW, Munro MHG, Gussio R, Hamel E (2006) Mol Pharmacol 70:1866–1875CrossRefGoogle Scholar
  14. 14.
    Jordan MA, Kamath K, Manna T, Okouneva T, Miller HP, Davis C, Littlefield BA, Wilson L (2005) Mol Cancer Ther 4:1086–1095CrossRefGoogle Scholar
  15. 15.
    Overmoyer B (2008) Clin Breast Cancer 8:S61–S70CrossRefGoogle Scholar
  16. 16.
    Yu MJ, Zheng W, Seletsky BM, Littlefield BA, Kishi Y (2011) Annu Rep Med Chem 46:227–241CrossRefGoogle Scholar
  17. 17.
    Munro MHG, Blunt JW, Dumdei EJ, Hickford SJH, Lill RE, Li S, Battershill CN, Duckworth AR (1999) J Biotechnol 70:15–25CrossRefGoogle Scholar
  18. 18.
    Aicher TD, Buszek KR, Fang FG, Forsyth CJ, Jung SH, Kishi Y, Matelich MC, Scola PM, Spero DM, Yoon SK (1992) J Am Chem Soc 114:3162–3164CrossRefGoogle Scholar
  19. 19.
    Yu MJ, Kishi Y, Littlefield BA (2012) Discovery of E7389, a fully synthetic macrocyclic ketone analog of halichondrin B. In: Cragg GM, Kingston DGI, Newman DJ (eds) Anticancer agents from natural products, 2nd edn. CRC Press, Boca Raton, pp 317–345Google Scholar
  20. 20.
    Jackson KL, Henderson JA, Motoyoshi H, Philips AJ (2009) Angew Chem Int Ed 48:2346–2350CrossRefGoogle Scholar
  21. 21.
    Ueda A, Yamamoto A, Kato D, Kishi Y (2014) J Am Chem Soc 136:5171–5176CrossRefGoogle Scholar
  22. 22.
    Hargarden GC, Guiry PJ (2007) Adv Synth Catal 349:2407–2424CrossRefGoogle Scholar
  23. 23.
    Towle MJ, Salvato KA, Wels BF, Aalfs KK, Zheng W, Seletsky BM, Zhu X, Lewis BM, Kishi Y, Yu MJ, Littlefield BA (2011) Cancer Res 71:496–505CrossRefGoogle Scholar
  24. 24.
    Wang Y, Habgood GJ, Christ WJ, Kishi Y, Littlefield BA, Yu MJ (2000) Bioorg Med Chem Lett 10:1029–1032CrossRefGoogle Scholar
  25. 25.
    Seletsky BM, Wang Y, Hawkins LD, Palme MH, Habgood GJ, DiPietro LV, Towle MJ, Salvato KA, Wels BF, Aalfs KK, Kishi Y, Littlefield BA, Yu MJ (2004) Bioorg Med Chem Lett 14:5547–5550CrossRefGoogle Scholar
  26. 26.
    Zheng W, Seletsky BM, Palme MH, Lydon PJ, Singer LA, Chase CE, Lemelin CE, Shen Y, Davis H, Tremblay L, Towle MJ, Salvato KA, Wels BF, Aalfs KK, Kishi Y, Littlefield BA, Yu MJ (2004) Bioorg Med Chem Lett 14:5551–5554CrossRefGoogle Scholar
  27. 27.
    Towle MJ, Salvato KA, Budrow J, Wels BF, Kuznetsov G, Aalfs KK, Welsh S, Zheng W, Seletsky BM, Palme MH, Habgood GJ, Singer LA, DiPietro LV, Wang Y, Chen JJ, Quincy DA, Davis A, Yoshimatsu K, Kishi Y, Yu MJ, Littlefield BA (2001) Cancer Res 61:1013–1021Google Scholar
  28. 28.
    Wang Y (2007) Drugs Future 32:681–698CrossRefGoogle Scholar
  29. 29.
    Ledford H (2010) Nature 468:608–609CrossRefGoogle Scholar
  30. 30.
    Littlefield BA, Palme M, Seletsky BM, Towle MJ, Yu MJ (1999) Macrocyclic analogs and methods of their use and preparation. PCT Int Appl WO 99/65894, 23 Dec 1999Google Scholar
  31. 31.
    Littlefield BA, Palme MH, Seletsky BM, Towle MJ, Yu MJ, Zheng W (2001) Macrocyclic analogs and methods of their use and preparation. US Patent 6,214,865, 10 April 2001Google Scholar
  32. 32.
    Stamos DP, Kishi Y (1996) Tetrahedron Lett 37:8643–8646CrossRefGoogle Scholar
  33. 33.
    Aicher TD, Kishi Y (1987) Tetrahedron Lett 28:3463–3466CrossRefGoogle Scholar
  34. 34.
    Kishi Y, Fang FG, Forsyth CJ, Scola PM, Yoon SK (1995) Synthesis of halichondrin B and norhalichondrin B. US Patent 5,436,238, 25 July 1995Google Scholar
  35. 35.
    Yu MJ, Zheng W, Seletsky BM (2013) Nat Prod Rep 30:1158–1164CrossRefGoogle Scholar
  36. 36.
    Smith AB, Chen SSY, Nelson FC, Reichert JM, Salvatore BA (1995) J Am Chem Soc 117:12013–12014CrossRefGoogle Scholar
  37. 37.
    Magnus PD (1977) Tetrahedron 33:2019–2045CrossRefGoogle Scholar
  38. 38.
    Meyer SD, Schreiber SL (1994) J Org Chem 59:7549–7552CrossRefGoogle Scholar
  39. 39.
    Littlefield BA, Palme MH, Seletsky BM, Towle MJ, Yu MJ, Zheng W (2002) Intermediate compounds for preparing macrocyclic analogs. US Patent 6,365,759, 2 April 2002Google Scholar
  40. 40.
    Wan ZK, Choi H, Kang FA, Nakajima K, Demeke D, Kishi Y (2002) Org Lett 25:4431–4434CrossRefGoogle Scholar
  41. 41.
    Austad B, Chase CE, Fang FG (2005) Intermediates for the preparation of halichondrin B. PCT Int Appl WO 2005/118565, 15 Dec 2005Google Scholar
  42. 42.
    Choi H, Nakajima K, Demeke D, Kang FA, Jun HS, Wan ZK, Kishi Y (2002) Org Lett 25:4435–4438CrossRefGoogle Scholar
  43. 43.
    Hu Y (2009) Halichondrin B analogs. PCT Int Appl WO 2009/124237, 8 Oct 2009Google Scholar
  44. 44.
    Austad BC, Calkins TL, Chase CE, Fang FG, Horstmann TE, Hu Y, Lewis BM, Niu X, Noland TA, Orr JD, Schnaderbeck MJ, Zhang H, Asakawa N, Asai N, Chiba H, Hasebe T, Hoshino Y, Ishizuka H, Kajima T, Kayano A, Komatsu Y, Kubota M, Kuroda H, Miyazawa M, Tagami K, Watanabe T (2013) Synlett 24:333–337CrossRefGoogle Scholar
  45. 45.
    Chiba H, Fukuyama T, Takigawa T, Komatsu Y (2012) Microreactor process for halichondrin B analog synthesis. PCT Int Appl WO 2012/147900, 1 Nov 2012Google Scholar
  46. 46.
    Hu Y, Zhang H, Chiba H, Komatsu Y (2015) Methods useful in the synthesis of halichondrin B analogs. PCT Int Appl WO 2015/085193, 11 June 2015Google Scholar
  47. 47.
    Fukuyama T, Chiba H, Kuroda H, Takigawa T, Kayano A, Tagami K (2016) Org Process Res Dev 20:503–509Google Scholar
  48. 48.
    Inanga K, Fukuyama T, Kubota M, Komatsu Y, Chiba H, Kayano A, Tagami K (2015) Org Lett 17:3158–3161CrossRefGoogle Scholar
  49. 49.
    Chase CE, Fang F, Lewis BM, Wilkie GD, Schnaderbeck MJ, Zhu X (2013) Synlett 24:323–326CrossRefGoogle Scholar
  50. 50.
    Rajendran A, Paredes G, Mazzotti M (2009) J Chromatogr A 1216:709–738CrossRefGoogle Scholar
  51. 51.
    Tokunaga M, Larrow JF, Kakiuchi F, Jacobsen EN (1997) Science 277:936–938CrossRefGoogle Scholar
  52. 52.
    Kurosu M, Lin MH, Kishi Y (2004) J Am Chem Soc 126:12248–12249CrossRefGoogle Scholar
  53. 53.
    Choi H, Demeke D, Kang FA, Kishi Y, Nakajima K, Nowak P, Wan ZK, Xie C (2003) Pure Appl Chem 75:1–17CrossRefGoogle Scholar
  54. 54.
    Austad BC, Benayoud F, Calkins TL, Campagna S, Chase CE, Choi H, Christ W, Costanzo R, Cutter J, Endo A, Fang FG, Hu Y, Lewis BM, Lewis MD, McKenna S, Noland TA, Orr JD, Pesant M, Schnaderbeck MJ, Wilkie GD, Abe T, Asai N, Asai Y, Kayano A, Kimoto Y, Komatsu Y, Kubota M, Kuroda H, Mizuno M, Nakamura T, Omae T, Ozeki N, Suzuki T, Takigawa T, Watanabe T, Yoshizawa K (2013) Synlett 24:327–332CrossRefGoogle Scholar
  55. 55.
    Stork G, Kahne DE (1983) J Am Chem Soc 105:1072–1073CrossRefGoogle Scholar
  56. 56.
    Crabtree RH, Felkin H, Fellebeen-Khan T, Morris GE (1979) J Organomet Chem 168:183–195CrossRefGoogle Scholar
  57. 57.
    Yang YR, Kim DS, Kishi Y (2009) Org Lett 11:4516–4519CrossRefGoogle Scholar
  58. 58.
    Guo H, Dong CG, Kim DS, Urabe D, Wang J, Kim JT, Liu X, Sasaki T, Kishi Y (2009) J Am Chem Soc 131:15387–15393CrossRefGoogle Scholar
  59. 59.
    Liu X, Henderson JA, Sasaki T, Kishi Y (2009) J Am Chem Soc 131:16678–16680CrossRefGoogle Scholar
  60. 60.
    Liu S, Kim JT, Dong CG, Kishi Y (2009) Org Lett 11:4520–4523CrossRefGoogle Scholar
  61. 61.
    Kim DS, Dong CG, Kim JT, Guo H, Huang J, Tiseni PS, Kishi Y (2009) J Am Chem Soc 131:15636–15641CrossRefGoogle Scholar
  62. 62.
    Zhang Z, Huang J, Kishi Y (2008) Org Lett 10:3073–3076CrossRefGoogle Scholar
  63. 63.
    Dong CG, Henderson JA, Kaburagi Y, Sasaki T, Kim DS, Kim JT, Urabe D, Guo H, Kishi Y (2009) J Am Chem Soc 131:15642–15646CrossRefGoogle Scholar
  64. 64.
    Trost BM, Ball ZT (2003) J Am Chem Soc 125:30–31CrossRefGoogle Scholar
  65. 65.
    Trost BM, Ball ZT, Laemmerhold KM (2005) J Am Chem Soc 127:10028–10038CrossRefGoogle Scholar
  66. 66.
    Shan M, Kishi Y (2012) Org Lett 14:660–663CrossRefGoogle Scholar
  67. 67.
    Uguen D (1981) Bull Chim Soc Fr II:99–102Google Scholar
  68. 68.
    Liu L, Henderson JA, Yamamoto A, Brémond P, Kishi Y (2012) Org Lett 14:2262–2265CrossRefGoogle Scholar
  69. 69.
    Duan JJW, Kishi Y (1993) Tetrahedron Lett 34:7541–7544CrossRefGoogle Scholar
  70. 70.
    Shiina I, Katoh T, Nagai S, Hashizume M (2009) Chem Rec 9:305–320CrossRefGoogle Scholar
  71. 71.
    Shiina I, Kubota M, Ibuka R (2002) Tetrahedron Lett 43:7535–7539CrossRefGoogle Scholar
  72. 72.
    Namba K, Yun H-S, Kishi Y (2004) J Am Chem Soc 126:7770–7771CrossRefGoogle Scholar
  73. 73.
    Kaburagi Y, Kishi Y (2007) Org Lett 9:723–726CrossRefGoogle Scholar
  74. 74.
    Yan W, Li J, Kishi Y (2015) J Am Chem Soc 137:6219–6225CrossRefGoogle Scholar
  75. 75.
    Li J, Yan W, Kishi Y (2015) J Am Chem Soc 137:6226–6231CrossRefGoogle Scholar
  76. 76.
    Blanchette MA, Choy W, Davis JT, Essenfeld AP, Masamune S, Roush WR, Sakai T (1984) Tetrahedron Lett 25:2183–2186CrossRefGoogle Scholar
  77. 77.
    Bernet B, Vasella A (1979) Helv Chim Acta 62:1990–2016CrossRefGoogle Scholar
  78. 78.
    Belanger F, Chase CE, Endo A, Fang FG, Li J, Mathieu SR, Wilcoxen AZ, Zhang H (2015) Angew Chem Int Ed 54:5108–5111CrossRefGoogle Scholar
  79. 79.
    Liu KKC, Sakya SM, O’Donnell CJ, Flick AC, Ding HX (2012) Bioorg Med Chem 20:1155–1174CrossRefGoogle Scholar
  80. 80.
    Chase C, Endo A, Fang FG, Li J (2009) Intermediates and methods for the synthesis of halichondrin B analogs. PCT Int Appl WO 2009/046308, 9 April 2009Google Scholar
  81. 81.
    Kim D-S, Choi H-W, Chase CE, Lee J (2015) Macrocyclization reactions and intermediates useful in the synthesis of analogs of halichondrin B. PCT Int Appl WO 2015/066729, 7 May 2015Google Scholar
  82. 82.
    Garber SB, Kingsbury JS, Gray BL, Hoveyda AH (2000) J Am Chem Soc 122:8168–8179CrossRefGoogle Scholar
  83. 83.
    Schauer DJ, Helquist P (2006) Synthesis 3654–3660Google Scholar
  84. 84.
    Pirrung MC, Biswas G, Ibarra-Rivera TR (2010) Org Lett 12:2402–2405CrossRefGoogle Scholar
  85. 85.
    Lin JH, Yamazaki M (2003) Drug Metab Rev 35:417–454CrossRefGoogle Scholar
  86. 86.
    Goda K, Bacso Z, Szabo G (2009) Curr Cancer Drug Targets 9:281–297CrossRefGoogle Scholar
  87. 87.
    Chan LMS, Lowes S, Hirst BH (2004) Eur J Pharm Sci 21:25–51CrossRefGoogle Scholar
  88. 88.
    Narayan S, Carlson EM, Cheng H, Du H, Hu Y, Jiang Y, Lewis BM, Seletsky BM, Tendyke K, Zhang H, Zheng W, Littlefield BA, Towle MJ, Yu MJ (2011) Bioorg Med Chem Lett 21:1630–1633CrossRefGoogle Scholar
  89. 89.
    Narayan S, Carlson EM, Cheng H, Condon K, Du H, Eckley S, Hu Y, Jiang Y, Kumar V, Lewis BM, Saxton P, Schuck E, Seletsky BM, Tendyke K, Zhang H, Zheng W, Littlefield BA, Towle MJ, Yu MJ (2011) Bioorg Med Chem Lett 21:1634–1638CrossRefGoogle Scholar
  90. 90.
    Yu MJ, Zheng W, Tendyke K (2012) Bioorg Med Chem Lett 22:7363–7366CrossRefGoogle Scholar
  91. 91.
    Narayan S, Carlson EM, Cheng H, Condon K, Du H, Eckley S, Hu Y, Jiang Y, Kumar V, Lewis BM, Saxton P, Schuck E, Seletsky BM, Tendyke K, Zhang H, Zheng W, Littlefield BA, Towle MJ, Yu MJ (2011) Bioorg Med Chem Lett 21:1639–1643CrossRefGoogle Scholar
  92. 92.
    Dasari B, Jimmidi R, Arya P (2015) Eur J Med Chem 94:497–508CrossRefGoogle Scholar
  93. 93.
    Rudolph A, Alberico D, Jordan R, Pan M, Souza FES, Gorin B (2013) Tetrahedron Lett 54:7059–7061CrossRefGoogle Scholar
  94. 94.
    Okabe M, Sun RC, Zenchoff GB (1991) J Org Chem 56:4392–4397CrossRefGoogle Scholar
  95. 95.
    Jimmidi R, Gudru SKR, Arya P (2015) Org Lett 17:468–471CrossRefGoogle Scholar
  96. 96.
    Sabitha G, Chandrashekhar G, Yadav JS, Rachineni K, Jagadeesh B (2012) RSC Adv 2:10157–10159CrossRefGoogle Scholar
  97. 97.
    Yadav JS, Reddy CN, Sabitha G (2012) Tetrahedron Lett 53:2504–2507CrossRefGoogle Scholar
  98. 98.
    Hanawa H, Hahimoto T, Maruoka K (2003) J Am Chem Soc 125:1708–1709CrossRefGoogle Scholar
  99. 99.
    Murthy AS, Mahipal B, Chandrasekhar S (2012) Eur J Org Chem 6959–6966Google Scholar
  100. 100.
    Chandrasekhar S, Yaragorla SR, Sreelakshmi L, Reddy CR (2008) Tetrahedron 64:5174–5183CrossRefGoogle Scholar
  101. 101.
    Hodgson DM, Salik S (2012) Org Lett 14:4402–4405CrossRefGoogle Scholar
  102. 102.
    Scholl M, Ding S, Lee CW, Grubbs HR (1999) Org Lett 1:953–956CrossRefGoogle Scholar
  103. 103.
    Lavanya N, Kiranmai N, Mainkar PS, Chandrasekhar S (2015) Tetrahedron Lett 56:4283–4285CrossRefGoogle Scholar
  104. 104.
    Liu J, Liu Y, Zhang X, Zhang C, Gao Y, Wang L, Du Y (2012) J Org Chem 77:9718–9723CrossRefGoogle Scholar
  105. 105.
    Still WC, Gennari C (1983) Tetrahedron Lett 24:4405–4408CrossRefGoogle Scholar
  106. 106.
    Murthy AS, Chandrasekhar S (2015) Tetrahedron Lett 56:4280–4282CrossRefGoogle Scholar
  107. 107.
    Bergeron-Brlek M, Teoh T, Britton R (2013) Org Lett 15:3554–3557CrossRefGoogle Scholar
  108. 108.
    Chavan LN, Chegondi R, Chandrasekhar S (2015) Tetrahedron Lett 56:4286–4288CrossRefGoogle Scholar
  109. 109.
    Goel S, Mita AC, Mita M, Rowinsky EK, Chu QS, Wong N, Desjardins C, Fang F, Jansen M, Shuster DE, Mani S, Takimoto CH (2009) Clin Cancer Res 15:4207–4212CrossRefGoogle Scholar
  110. 110.
    Tan AR, Rubin EH, Walton DC, Shuster DE, Wong NY, Fang F, Ashworth S, Rosen LS (2009) Clin Cancer Res 15:4213–4219CrossRefGoogle Scholar
  111. 111.
    Vahdat L, Pruitt B, Fabian CJ, Rivera RR, Smith DA, Tan-Chiu E, Wright J, Tan AR, DaCosta NA, Chuang E, Smith J, O’Shaughnessy J, Shuster DE, Meneses NL, Chandrawansa K, Fang F, Cole PE, Ashworth S, Blum JL (2009) J Clin Oncol 27:2954–2961CrossRefGoogle Scholar
  112. 112.
    Cortes J, Vahdat L, Blum JL, Twelves C, Campone M, Roché H, Bachelot T, Awada A, Pardaens R, Goncalves A, Shuster DE, Wanders J, Fang F, Gurnani R, Richmond E, Cole PE, Ashworth S, Allison MA (2010) J Clin Oncol 28:3922–3928CrossRefGoogle Scholar
  113. 113.
    Cortes J, O’Shaughnessy J, Loesch D, Blum JL, Vahdat LT, Petrakova K, Chollet P, Manikasd A, Diéras V, Delozier T, Vladimirov V, Cardoso F, Koh H, Bougnoux P, Dutcus CE, Seegobin S, Mir D, Meneses N, Wanders J, Twelves C (2011) Lancet 377:914–923CrossRefGoogle Scholar
  114. 114.
    Aftimos P, Awada A (2011) Adv Ther 28:973–985CrossRefGoogle Scholar
  115. 115.
    Gaducci A, Guerrieri ME (2015) Expert Opin Pharmacother 16:335–346Google Scholar
  116. 116.
    Thara E, Gitlitz BJ (2014) Future Oncol 10:1913–1924CrossRefGoogle Scholar
  117. 117.
    Koczywas M, Frankel PH, Synold TW, Lenz H-J, Mortimer JE, El-Khoueiry AB, Gandara DR, Cristea MC, Chung VM, Lim D, Reckamp KL, Lau DH, Doyle LA, Ruel C, Carroll MI, Newman EM (2014) Br J Cancer 111:2268–2274CrossRefGoogle Scholar
  118. 118.
    O’Rourke B, Yang C-PH, Sharp D, Horwitz SB (2014) Cell Cycle 13:3218–3221CrossRefGoogle Scholar
  119. 119.
    Yoshida T, Ozawa Y, Kimura T, Sato Y, Kuznetsov G, Xu S, Uesugi M, Agoulnik S, Taylor N, Funahashi Y, Matsui J (2014) Br J Cancer 110:1497–1505CrossRefGoogle Scholar
  120. 120.
    Fukuyama T, Chiba H, Takigawa T, Komatsu Y, Kayano A, Tagami K (2016) Org Process Res Dev 20:100–104CrossRefGoogle Scholar

Copyright information

© Springer International Publishing Switzerland 2016

Authors and Affiliations

  1. 1.Sanofi-Aventis Deutschland GmbH, R&D LGCR/ChemistryFrankfurt am MainGermany

Personalised recommendations