Total Synthesis of Antascomicin B

The structurally enticing antascomicin B (1), which exhibits potent immunosuppressant‐antagonizing properties, has a complex polyketide structure. Key steps in its enantioselective total synthesis include a transannular catechol‐templated Dieckmann reaction to assemble the challenging tricarbonyl fu...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 44; no. 18; pp. 2732 - 2737
Main Authors Brittain, Dominic E. A., Griffiths-Jones, Charlotte M., Linder, Michael R., Smith, Martin D., McCusker, Catherine, Barlow, Jaqueline S., Akiyama, Ryo, Yasuda, Kosuke, Ley, Steven V.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 29.04.2005
WILEY‐VCH Verlag
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
macrocycles
Molecular Structure
natural products
oxidation
Physical Sciences
Science & Technology
Tacrolimus - analogs & derivatives
Tacrolimus - chemical synthesis
Tacrolimus - chemistry
Tin Compounds - chemistry
total synthesis
ORGANIC-SYNTHESIS
MOLECULAR-DYNAMICS
RING KETONE SYNTHESIS
LEWIS-ACID
oxidation
ALDEHYDES
TAUTOMERIC PHENOMENON
natural products
IMMUNOPHILIN FKBP
macrocycles
NAPHTHALENE DIANION
total synthesis
POTENT IMMUNOSUPPRESSANT FK506
ARENE-CATALYZED LITHIATION
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Summary:The structurally enticing antascomicin B (1), which exhibits potent immunosuppressant‐antagonizing properties, has a complex polyketide structure. Key steps in its enantioselective total synthesis include a transannular catechol‐templated Dieckmann reaction to assemble the challenging tricarbonyl functionality and a butanediacetal‐directed allylation.
Bibliography:The authors would like to thank Novartis for the Novartis Research Fellowship (to S.V.L.), Trinity College, Cambridge for a Junior Research Fellowship (to D.E.A.B.), Pembroke College, Cambridge and the Royal Society for fellowships (to M.D.S.), the EPSRC (to C.M.G.-J., M.R.L., C.M., and D.E.A.B.), Tanabe Seiyaku Co., Ltd. for a postdoctoral fellowship (to K.Y.), and the Japanese Society for the Promotion of Sciences (to R.A.). The authors would also like to acknowledge the contribution of Prof. Hidenori Watanabe (University of Tokyo; Cambridge 1998-2000) whose studies on a related system were invaluable in the development of the macrocyclization method described herein.
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ArticleID:ANIE200500174
The authors would like to thank Novartis for the Novartis Research Fellowship (to S.V.L.), Trinity College, Cambridge for a Junior Research Fellowship (to D.E.A.B.), Pembroke College, Cambridge and the Royal Society for fellowships (to M.D.S.), the EPSRC (to C.M.G.‐J., M.R.L., C.M., and D.E.A.B.), Tanabe Seiyaku Co., Ltd. for a postdoctoral fellowship (to K.Y.), and the Japanese Society for the Promotion of Sciences (to R.A.). The authors would also like to acknowledge the contribution of Prof. Hidenori Watanabe (University of Tokyo; Cambridge 1998–2000) whose studies on a related system were invaluable in the development of the macrocyclization method described herein.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200500174