Abstract
The bryostatins are a family of marine natural products originally isolated from the bryozoan Bugula neritina by Pettit and coworkers in the course of their search for new antineoplastic agents derived from marine organisms [1]. Later, during a large-scale isolation, 18 g of bryostatin 1, the first discovered and most naturally abundant member of this family, was obtained from a collection of 10,000 gallons of wet bryozoan [2].
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For current information, see: http://clinicaltrials.gov
References
Pettit GR, Herald CL, Doubek DL, Herald DL, Arnold E, Clardy J (1982) J Am Chem Soc 104:6846
Schaufelberger DE, Koleck MP, Beutler JA, Vatakis AM, Alvarado AB, Andrews P, Marzo LV, Muschik GM, Roach J, Ross JT, Lebherz WB, Reeves MP, Eberwein RM, Rodgers LL, Testerman RP, Snader KM, Forenza S (1991) J Nat Prod 54:1265
Hildebrand M, Waggoner LE, Liu H, Sudek S, Allen S, Anderson C, Sherman DH, Haygood M (2004) Chem Biol 11:1543
For selected reviews encompassing the biological properties of the bryostatins, see: (a) Hale KJ, Hummersone MG, Manaviazar S, Frigerio M (2002) Nat Prod Rep 19:413; (b) Kortmansky J, Schwartz GK (2003) Cancer Invest 21:924; (c) Wender PA, Baryza JL, Hilinski MK, Horan JC, Kan C, Verma VA (2007) Beyond natural products: synthetic analogs of bryostatin 1. In: Huang Z (ed) Drug discovery research: new frontiers in the post-genomic era, Wiley, Hoboken, NJ, pp 127–162; (d) Hale KJ, Manaviazar S (2010) Chem Asian J 5:704
Wall NR, Mohammad RM, Al-Katib AM (1999) Leuk Res 23:881
Elgie AW, Sargent JM, Alton P, Peters GJ, Noordhuis P, Williamson CJ, Taylor CG (1998) Leuk Res 22:373
Oz HS, Hughes WT, Rehg JE, Thomas EK (2000) Microb Pathog 29:187
Gescher A, Stanwell C, Dale I (1994) Cancer Top 9:3
(a) Nishizuka Y (1992) Science 258:607; (b) Caponigro F, French RC, Kaye SB (1997) Anti-Cancer Drugs 8:26
Castagna M, Takai Y, Kaibuchi K, Sano K, Kikkawa U, Nishizuka YJ (1982) Biol Chem 257:7874
Blumberg PM, Pettit GR (1992) In: Krosgaard-Larsen P, Christensen CB, Kodof H (eds) New leads and targets in drug research, Munksgaard, Copenhagen, pp 273–285
(a) Dowlati A, Lazarus HM, Hartman P, Jacobberger JW, Whitacre C, Gerson SL, Ksenich P, Cooper BW, Frisa PS, Gottlieb M, Murgo AJ, Remick SC (2003) Clin Cancer Res 9:5929; (b) Barr PM, Lazarus HM, Cooper BW, Schluchter MD, Panneerselvam A, Jacobberger JW, Hsu JW, Janakiraman N, Simic A, Dowlati A, Remick SC (2009) Am J Hematol 84:484; (c) Ajani JA, Jiang Y, Faust J, Chang BB, Ho L, Yao JC, Rousey S, Dakhil S, Cherny RC, Craig C, Bleyer A (2006) Invest New Drugs 24:353
Hongpaisan J, Alkon DL (2007) Proc Natl Acad Sci USA 104:19571
Sun M-K, Alkon DL (2005) Eur J Pharmacol 512:43
(a) Etcheberrigaray R, Tan M, Dewachter I, Kuiperi C, Van der Auwera I, Wera S, Qiao L, Bank B, Nelson TJ, Kozikowski AP, Van Leuven F, Alkon DL (2004) Proc Natl Acad Sci USA 101:11141; (b) Alkon DL, Sun M-K, Nelson TJ (2007) Trends Pharmacol Sci 28:51
Sun M-K, Alkon DL (2006) CNS Drug Rev 12:1
(a) Sun M-K, Hongpaisan J, Nelson TJ, Alkon DL (2008) Proc Natl Acad Sci USA 105:13620; (b) Sun M-K, Hongpaisan J, Alkon DL (2009) Proc Natl Acad Sci USA 106:14676
(a) Perez M, de Vinuesa AG, Sanchez-Duffhues G, Marquez N, Bellido M, Munoz-Fernandez MA, Moreno S, Castor TP, Calzado MA, Munoz E (2010) Curr HIV Res 8:418; (b) Mehla R, Bivalkar-Mehla S, Zhang R, Handy I, Albrecht H, Giri S, Nagarkatti P, Nagarkatti M, Chauhan A (2010) PLos One 5:e11160
Wender PA, Cribbs CM, Koehler KF, Sharkey NA, Herald CL, Kamano Y, Pettit GR, Blumberg PM (1988) Proc Natl Acad Sci USA 85:7197
For selected examples of Wender’s bryostatin analogues, see: (a) Wender PA, De Brabander J, Harran PG, Jiminez J-M, Koehler MFT, Lippa B, Park C-M, Shiozaki M (1998) J Am Chem Soc 120:4534; (b) Wender PA, De Brabander J, Harran PG, Jiminez J-M, Koehler MFT, Lippa B, Park C-M, Siedenbiedel C, Pettit GR (1998) Proc Natl Acad Sci USA 95:6624; (c) Wender PA, Baryza JL, Bennett CE, Bi FC, Brenner SE, Clarke MO, Horan JC, Kan C, Lacôte E, Lippa BS, Nell PG, Turner TM (2002) J Am Chem Soc 124:13648; (d) Wender PA, Baryza JL, Hilinski MK, Horan JC, Kan C, Verma VA (2007) In: Huang Z (ed) Drug discovery research: new frontiers in the post-genomic era, Wiley, Hoboken, NJ, pp 127–162; (e) Wender PA, DeChristopher BA, Schrier AJ (2008) J Am Chem Soc 130:6658; (f) Wender PA, Verma VA (2006) Org Lett 8:1893; (g) Wender PA, Baryza JL, Brenner SE, DeChristopher BA, Loy BA, Schrier AJ, Verma VA (2011) Proc Natl Acad Sci USA 108:6721
For selected examples of Keck’s bryostatin analogues, see: (a) Keck GE, Truong AP (2005) Org Lett 7:2153; (b) Keck GE, Kraft MB, Truong AP, Li W, Sanchez CC, Kedei N, Lewin N, Blumberg PM (2008) J Am Chem Soc 130:6660; (c) Keck GE, Poudel YB, Welch DS, Kraft MB, Truong AP, Stephens JC, Kedei N, Lewin NE, Blumberg PM (2009) Org Lett 11:593; (d) Keck GE, Li W, Kraft MB, Kedei N, Lewin NE, Blumberg PM (2009) Org Lett 11:2277; (e) Keck GE, Poudel YB, Rudra A, Stephens JC, Kedei N, Lewin NE, Peach ML, Blumberg PM (2010) Angew Chem Int Ed 49:4580
(a) Sudek S, Lopanik NB, Waggoner L E, Hildebrand M, Anderson C, Liu H, Patel A, Sherman DH, Haygood MG (2007) J Nat Prod 70:67; (b) Lopanik NB, Shields J, Buchholz TJ, Rath CM, Hothersall J, Haygood MG, Hakansson K, Thomas CM, Sherman DH (2008) Chem Biol 15:1175; (c) Trindade-Silva AE, Lim-Fong GE, Sharp KH, Haygood MG (2010) Curr Opin Biotechnol 21:834
(a) Kageyama M, Tamura T, Nantz M, Roberts JC, Somfai P, Whritenour DC, Masamune S (1990) J Am Chem Soc 112:7407; (b) Masamune S (1988) Pure Appl Chem 60:1587
(a) Evans DA, Carter PH, Carreira EM, Prunet JA, Charette AB, Lautens M (1998) Angew Chem Int Ed 37:2354; (b) Evans DA, Carter PH, Carreira EM, Charette AB, Prunet JA, Lautens M (1999) J Am Chem Soc 121:7540
(a) Ohmori K, Ogawa Y, Obitsu T, Ishikawa Y, Nishiyama S, Yamamura S (2000) Angew Chem Int Ed 39:2290; (b) Ohmori K (2004) Bull Chem Soc Jpn 77:875
Trost BM, Dong G (2008) Nature 456:485
Keck GE, Poudel YB, Cummins TJ, Rudra A, Covel JA (2011) J Am Chem Soc 133:744
Wender PA, Schrier AJ (2011) J Am Chem Soc 133:9228
Lu Y, Woo SK, Krische MJ (2011) J Am Chem Soc 133:13876
Manaviazar S, Frigerio M, Bhatia GS, Hummersone MG, Aliev AE, Hale KJ (2006) Org Lett 8:4477
Trost BM, Dong G (2010) J Am Chem Soc 132:16403
Green AP, Lee ATL, Thomas EJ (2011) Chem Commun 47:7200
Masamune S, Sato T, Kim B-M, Wollmann TA (1986) J Am Chem Soc 108:8279
(a) Julia M, Paris JM (1973) Tetrahedron Lett 14:4833; (b) Kocienski PJ, Lythgoe B, Ruston S (1978) J Chem Soc Perk T 1 829
(a) Katsuki T, Sharpless KB (1980) J Am Chem Soc 102:5974; (b) Rossiter BE, Katsuki T, Sharpless KB (1981) J Am Chem Soc 103:464; (c) Gao Y, Hanson RM, Klunder JM, Ko SY, Masamune H, Sharpless KB (1987) J Am Chem Soc 109:5765
Corey EJ, Katzenellenbogen JA, Posner GH (1967) J Am Chem Soc 89:4245
Piers E, Morton HE (1980) J Org Chem 45:4263
(a) Tanaka K, Ohta Y, Fuji K, Taga T (1993) Tetrahedron Lett 34:4071; (b) Tanaka K, Otsubo K, Fuji K (1996) Tetrahedron Lett 37:3735
Inanaga J, Hirata K, Saeki H, Katsuki T, Yamaguchi M (1979) Bull Soc Chem Jpn 52:1989
Evans DA, Sjogren EB, Weber AE, Conn RE (1987) Tetrahedron Lett 28:39
Evans DA, Chapman KT, Carreira E (1988) J Am Chem Soc 110:3560
(a) Ramachandran PV, Xu W-C, Brown HC (1996) Tetrahedron Lett 37:4911; (b) Paterson I, Goodman JM, Lister MA, Schumann RC, McClure CK, Norcross RD (1990) Tetrahedron 46:4663
Evans DA, Hoveyda AH (1990) J Am Chem Soc 112:6447
Evans DA, Murry JA, Kozlowski MC (1996) J Am Chem Soc 118:5814
Danishefsky S, Kobayashi S, Kerwin Jr JF (1982) J Org Chem 47:1981
Demuth M, Palomer A, Sluma H-D, Dey AK, Krüger C, Tsay Y-H (1986) Angew Chem Int Ed 25:1117
(a) Zinner H, Wulf G, Heinatz R (1964) Chem Ber 97:3536; (b) Copeland C, Stick RV (1977) Aust J Chem 30:1269; (c) Trost BM, Klun TP (1981) J Am Chem Soc 103:1864
Corey EJ, Fuchs PL (1972) Tetrahedron Lett 13:3769
(a) Ohmori K, Nishiyama S, Yamamura S (1995) Tetrahedron Lett 36:6519; (b) Kolb HC, VanNieuwenhze MS, Sharpless KB (1994) Chem Rev 94:2483
Trost BM, Matsubara S, Caringi JJ (1989) J Am Chem Soc 111:8745
Liu Y, Song F, Song Z, Liu M, Yan B (2005) Org Lett 5409
Trost BM, Yang H, Wuitschik G (2005) Org Lett 7:4761
Brown HC, Jadhav PK (1983) J Am Chem Soc 105:2092
Roth GJ, Liepold B, Müller SG, Bestmann HJ (2004) Synthesis 59
(a) Keck GE, Covel JA, Schiff T, Yu T (2002) Org Lett 4:1189; (b) Yu C-M, Lee J-Y, So B, Hong J (2002) Angew Chem Int Ed 41:161
Keck GE, Welch DS, Poudel YB (2006) Tetrahedron Lett 47:8267
(a) Keck GE, Tarbet KH, Geraci LS (1993) J Am Chem Soc 115:8467; (b) Costa AL, Piazza MG, Tagliavini E, Trombini C, Umani-Ronchi A (1993) J Am Chem Soc 115:7001
(a) Mukaiyama T, Narasaka K, Banno K (1973) Chem Lett 2:1011; (b) Mukaiyama T, Izawa T, Saigo K (1974) Chem Lett 3:323; (c) Mukaiyama T, Banno K, Narasaka K (1974) J Am Chem Soc 96:7503
(a) Iyer K, Rainier JD (2007) J Am Chem Soc 129:12604; (b) Nicolaou KC, Postema MHD, Claiborne CF (1996) J Am Chem Soc 118:1565; (c) Nicolaou KC, Postema MHD, Yue EW, Nadin A (1996) J Am Chem Soc 118:10335
Okazoe T, Takai K, Utimoto K (1987) J Am Chem Soc 109:951
For selected reviews, see: (a) Patman RL, Bower JF, Kim IS, Krische MJ (2008) Aldrichim Acta 41:95; (b) Bower JF, Kim IS, Patman RL, Krische MJ (2009) Angew Chem Int Ed 48:34; (c) Bower JF, Krische MJ (2011) Top Organomet Chem 43:107; (d) Hassan A, Krische MJ (2011) Org Process Res Dev 15:1236
(a) Lu Y, Kim IS, Hassan A, Del Valle DJ, Krische MJ (2009) Angew Chem Int Ed 48:5018; (b) Han SB, Hassan A, Kim I-S, Krische MJ (2010) J Am Chem Soc 132:15559; (c) Kumpulainen ETT, Kang B, Krische MJ (2011) Org Lett 13:2484; (d) Gao X, Han H, Krische MJ (2011) J Am Chem Soc 133:12795
(a) Cho C-W, Krische MJ (2006) Org Lett 8:891; (b) Lu Y, Krische MJ (2009) Org Lett 11:3108
(a) Han SB, Kim IS, Han H, Krische MJ (2009) J Am Chem Soc 131:6916; (b) Itoh J, Han SB, Krische MJ (2009) Angew Chem Int Ed 48:6313; (c) Bechem B, Patman RL, Hashmi ASK, Krische MJ (2010) J Org Chem 75:1795
(a) Kim IS, Ngai M-Y, Krische MJ (2008) J Am Chem Soc 130:6340; (b) Kim IS, Ngai M-Y, Krische MJ (2008) J Am Chem Soc 130:14891; (c) Hassan A, Lu Y, Krische MJ (2009) Org Lett 11:3112
(a) Hong Y-T, Cho C-W, Skucas E, Krische MJ (2007) Org Lett 9:3745; (b) Komanduri V, Krische MJ (2006) J Am Chem Soc 128:16448
For amplification of enantiomeric enrichment in the generation of C2-symmetric compounds, see: (a) Kogure T, Eliel EL (1984) J Org Chem 49:576; (b) Midland MM, Gabriel J (1985) J Org Chem 50:1143
(a) Smith AB III, Minbiole KP, Verhoest PR, Schelhaas M (2001) J Am Chem Soc 123:10942; (b) Rychnovsky SD, Griesgraber G, Powers JP (2000) Org Synth 77:1
Trost BM, Yang H, Thiel OR, Frontier AJ, Brindle CS (2007) J Am Chem Soc 129:2206
For a similar enolization-reduction sequence, see: Lovchik MA, Goeke A, Frater G (2007) J Org Chem 72:2427
Kornblum N, Frazier HW (1966) J Am Chem Soc 88:865
Almendros P, Rae A, Thomas EJ (2000) Tetrahedron Lett 41:9565
Nicolaou KC, Estrada AA, Zak M, Lee SH, Safina BS (2005) Angew Chem Int Ed 44:1378
For chemoselective Johnson–Lemieux oxidation of terminal olefins, see: (a) White JD, Kuntiyong P, Lee TH (2006) Org Lett 8:6039; (b) BouzBouz S, Cossy J (2003) Org Lett 5:3029
(a) Corey EJ, Gilman NW, Ganem BE (1968) J Am Chem Soc 90:5616; (b) Corey EJ, Katzenellenbogen JA, Gilman NW, Roman SA, Erickson BW (1968) J Am Chem Soc 90: 5618; (c) Gilman NW (1971) Chem Commun 733
Maki BE, Scheidt KA (2008) Org Lett 10:4331
For an overview of “redox economy” in organic synthesis, see: Baran PS, Hoffmann RW, Burns NZ (2009) Angew Chem Int Ed 48:2854
“The ideal synthesis creates a complex skeleton… in a sequence only of successive construction reactions involving no intermediary refunctionalizations, and leading directly to the structure of the target, not only its skeleton but also its correctly placed functionality.” Hendrickson JB (1975) J Am Chem Soc 97:5784
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Lu, Y., Krische, M.J. (2012). Bryostatin 7. In: Li, J., Corey, E. (eds) Total Synthesis of Natural Products. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-34065-9_5
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