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Total synthesis of sannanine and analogues thereof

  • Badher Naveen
  • Rajagopal Nagarajan
Regular Article
  • 102 Downloads

Abstract

The first total synthesis of Sannanine has been accomplished with an overall 30% yield in a concise manner. The key strategies involve Friedländer quinoline synthesis, demethylation, in situ oxidation and amination process.

Graphical Abstract

The first total synthesis of Sannanine has been accomplished with an overall 30% yield in a concise manner. The key strategies involve Friedländer quinoline synthesis, demethylation, in situ oxidation and amination processes.

Keywords

Total synthesis natural products Friedländer synthesis sannanine 

Notes

Acknowledgements

BN thanks to the UGC-SRF for fellowship. Both RN and BN acknowledge DST-SERB project number EMR/2016/007015/OC for the funding.

References

  1. 1.
    (a) Porter T H, Bowman C M and Folkers K 1973 antimetabolites of Coenzyme Q. 16. New Alkylmercaptoquinones Having Antimalarial Curative Activity J. Med. Chem. 16 115; (b) Rao K V, Biemann K and Woodward R B 1963 Studies of the Cycloheptatriene-Norcaradiene Isomerism in Some Novel Steroids J. Am. Chem. Soc. 85 2532; (c) Doyle T W, Balitz D M, Grulich R E, Nettleton D E, Gould S J, Tann C-H and Moews A E 1981 Structure Determination of Lavendamycin – a new Antitumor Antibiotic from Streptomyces Lavendulae Tetrahedron Lett. 22 4595; (d) Boger D L, Yasuda M, Mitscher L A, Drake S D, Kitos S D, Kitos P A and Thompson S C 1987 Streptonigrin and Lavendamycin Partial Structures. Probes for the Minimum, Potent Pharmacophore of Streptonigrin, Lavendamycin, and Synthetic Quinoline-5,8-diones J. Med. Chem. 30 1918Google Scholar
  2. 2.
    (a) Fryatt T, Pettersson H I, Gardipee W T, Bray K C, Green S J, Salwin A M Z, Beall H D and Moody C J 2004 Novel Quinolinequinone Antitumor Agents: Structure-metabolism Studies with NAD(P)H: Quinone Xidoreductase (NQO1) Bioorg. Med. Chem. 12 1667; (b) Hargreaves R, David C L, Whitesell L and Skibo E B 2003 Design of Quinolinedione-Based Geldanamycin Analogues Bioorg. Med. Chem. Lett. 13 3075; (c) Argreaves R H J, David C L, Whitesell L J, LaBarbera D V, Jamil A, Chapuis J C and Skibo E B 2008 Discovery of Quinolinediones Exhibiting a Heat Shock Response and Angiogenesis Inhibition J. Med. Chem. 51 2492; (d) Behforouz M and Merriman R L 1995 Quinoline-5,8-diones and Methods of Using them USOO5712289A 1; (e) Pearce A N, Chia E W, Berridge M V, Clark G R, Harper J L, Larsen L, Maas E W, Page M J, Perry N B, Webb V L and Copp B R 2007 Anti-inflammatory Thiazine alkaloids Isolated from the New Zeeland Ascidian Aplidium sp.: Inhibitors of the Neutrophil Respiratory Burst in a Model of Gouty Arthritis J. Nat. Prod. 70 936Google Scholar
  3. 3.
    (a) Machura B, Switlicka A, Wolff M, Tanak D, Musio R, Polanski J and Kruszynki R 2011 Novel Tricarbonyl Rhenium Complexes of 5,8-Quinolinedione Derivatives Synthesis, Spectroscopic Characterisation, X-ray Structure and DFT Calculations J. Organomet. Chem. 696 731; (b) Yoshida K, Noma Y and Ueno Y 1994 Synthesis and Properties of 6-Substituted Quinoline-5,8-Dione Colour Formers J. Chem. Soc. Perkin T. 1 2521Google Scholar
  4. 4.
    (a) Seradj H, Cai W, Erasga N O, Chenault D V, Knuckles K A, Ragains J R and Behforouz M 2004, Total Synthesis of Novel 6-Substituted Lavendamycin Antitumer Agents Org. Lett. 6 473; (b) Blanco M D M, Avendano C and Menendez J C 1999 Concise synthesis of tetrahydro derivatives of the pyrido[2,3-b]acridine and pyrido[3,2-b]acridine ring systems Tetrahedron 55 12637Google Scholar
  5. 5.
    Li Y, Zheng D, Li Z, Han L, Cui X, Lang L, Li M, Wang Z, Zhao J and Huang X 2009 Sannanine, A New Cytotoxic Alkaloid From Streptomyces Sannanensis J. Antibiot. 62 647CrossRefGoogle Scholar
  6. 6.
    (a) Fernandez M, Lopez F, Tapia R and Valderrama J A 1989 Studies on the Synthesis of Fused Heterocycles From Ortho-Amino carbonyl Compounds Synth. Commun. 19 3087; (b) Blanco M D M, Avendano C, Cabezas N and Menendez J C 1993 A Friedlander Approach to 3-Substituted 2,5,8-\((1H)\)-Quinolinetrione Heterocycles 36 1387Google Scholar
  7. 7.
    Hargreaves R H J, David C L, Whitesell L J, LaBarbera D V, Jamil A, Chapuis J C and Skibo E B 2008 Discovery of Quinolinediones Exhibiting a Heat Shock Response and Angiogenesis Inhibition J. Med. Chem. 51 2492CrossRefGoogle Scholar

Copyright information

© Indian Academy of Sciences 2018

Authors and Affiliations

  1. 1.School of ChemistryUniversity of HyderabadHyderabadIndia

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