Total synthesis of sanglifehrin A

Academic Article

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Overview

related to degree

• Gray, David, Ph.D. in Chemistry, Scripps Research 1998 - 2003

authors

• Nicolaou, K.C.
• Xu, J. Y.
• Murphy, F.
• Barluenga, S.
• Baudoin, O.
• Wei, H. X.
• Gray, David
• Ohshima, T.

publication date

• 1999

journal

• Angewandte Chemie-International Edition  Journal

abstract

• The immunosuppressive agent sanglifehrin A has been prepared for the first time by total synthesis. The construction of the macrocyclic unit of the target molecule was achieved through a selective intramolecular Stille coupling, and the spirolactam unit by Paterson-aldol reactions. The final steps involve an intermolecular Stille coupling and the opening of the internal acetal unit. This convergent synthesis opens the way for the synthesis of libraries of novel sanglifehrin analogues for biological screening.

Research

keywords

• Stille couplings
• immunosuppressive agents
• natural products
• total synthesis

Identity

International Standard Serial Number (ISSN)

• 1433-7851

Digital Object Identifier (DOI)

• 10.1002/(sici)1521-3773(19990816)38:16<2447::aid-anie2447>3.0.co;2-o

PubMed ID

• 10458817

Additional Document Info

start page

• 2447

end page

• 2451

volume

• 38

issue

• 16