Total synthesis of clavaminol A, C and H

Zaed, A. and Sutherland, A. (2011) Total synthesis of clavaminol A, C and H. Organic and Biomolecular Chemistry, 9(23), pp. 8030-8037. (doi: 10.1039/C1OB06060K)

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Publisher's URL: http://dx.doi.org/10.1039/C1OB06060K

Abstract

The first total synthesis of clavaminol A and C, (2R,3S)-2-amino-3-alkanols from the Mediterranean ascidian Clavelina phlegraea has been achieved in 29% overall yield. The key step involved a palladium(II)-catalysed directed Overman rearrangement to create the C–N bond and install the erythro configuration while a one-pot, tributyltin hydride-mediated reduction allowed simultaneous formation of the methyl side-chain and N-acetyl group. Similarly, the first total synthesis of clavaminol H was completed in 48% overall yield using an approach that also provided the cytotoxic des-acetyl analogue.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Sutherland, Professor Andrew and Zaed, Mr Ahmed Mohamed
Authors: Zaed, A., and Sutherland, A.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Organic and Biomolecular Chemistry
ISSN:1477-0520

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