Issue 20, 2004

Phorboxazole B synthetic studies: construction of C(1–32) and C(33–46) subtargets

Abstract

The convergent syntheses of the C(1–32) and C(33–46) domains of phorboxazole B are described. An iterative cyclocondensation strategy exploited the Jacobsen hetero-Diels–Alder (HDA) reaction as a platform for the synthesis of both the C(5–9) and C(11–15) tetrahydropyran rings. The use of 2-silyloxydiene coupling partners bearing an increasing resemblance to the phorboxazole skeleton was found to lead to a reduction in diastereoselectivity, however, in the case of the C(11–15) ring. The coupling of aldehyde 21 and 2-silyloxydiene 20 by this route provided a C(1–32) fragment which was elaborated to the macrolide core of phorboxazole B. The synthesis of the C(33–46) domain involved a Nozaki–Kishi coupling of aldehyde 31 and vinyl iodide 39. The syntheses of 31 and 39 were highly diastereoselective: an Evans [Cu(Ph-pybox)](SbF6)2-catalysed Mukaiyama aldol reaction formed the cornerstone of the synthesis of 31 whilst a Nagao–Fujita acetate aldol reaction provided a convenient means of installing the sole stereogenic centre of 39.

Graphical abstract: Phorboxazole B synthetic studies: construction of C(1–32) and C(33–46) subtargets

Article information

Article type
Paper
Submitted
14 May 2004
Accepted
26 Aug 2004
First published
28 Sep 2004

Org. Biomol. Chem., 2004,2, 3026-3038

Phorboxazole B synthetic studies: construction of C(1–32) and C(33–46) subtargets

I. Paterson, A. Steven and C. A. Luckhurst, Org. Biomol. Chem., 2004, 2, 3026 DOI: 10.1039/B407240E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements