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Issue 13, 2005
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The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the AB-spiroacetal segment

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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

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Publication details

The article was received on 11 Apr 2005, accepted on 03 May 2005 and first published on 24 May 2005


Article type: Paper
DOI: 10.1039/B504146E
Citation: Org. Biomol. Chem., 2005,3, 2399-2409
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    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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