Issue 13, 2005

The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the AB-spiroacetal segment

Abstract

The convergent synthesis of the C1–C15 AB-spiroacetal subunit 2 of altohyrtin A/spongistatin 1 (1) is described. This highly stereocontrolled synthesis relies on matched boron aldol reactions of chiral methyl ketones, under Ipc2BCl mediation, to establish the C5, C9 and C11 stereocentres, and formation of the desired thermodynamic spiroacetal under acidic conditions. The scalable synthetic sequence developed provided access to multi-gram quantities of 2, thus enabling the successful completion of the total synthesis of altohyrtin A/spongistatin 1, as reported in Part 4.

Graphical abstract: The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the AB-spiroacetal segment

Supplementary files

Article information

Article type
Paper
Submitted
11 Apr 2005
Accepted
03 May 2005
First published
24 May 2005

Org. Biomol. Chem., 2005,3, 2399-2409

The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the AB-spiroacetal segment

I. Paterson, M. J. Coster, D. Y.-K. Chen, R. M. Oballa, D. J. Wallace and R. D. Norcross, Org. Biomol. Chem., 2005, 3, 2399 DOI: 10.1039/B504146E

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