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

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Abstract

Stereocontrolled syntheses of the C16–C28 CD-spiroacetal subunit of altohyrtin A/spongistatin 1 (1), relying on kinetic and thermodynamic control of the spiroacetal formation, are described. The kinetic control approach resulted in a slight preference (60 : 40) for the desired spiroacetal isomer. The thermodynamic approach allowed ready access to the desired spiroacetal 2 by acid-promoted equilibration, chromatographic separation of the C23 epimers and resubjection of the undesired isomer to the equilibration conditions. This scalable synthetic sequence provided multi-gram quantities of 2, thus enabling the successful completion of the total synthesis of altohyrtin A/spongistatin 1, as reported in Part 4 of this series.

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

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Article information


Submitted
22 Mar 2005
Accepted
03 May 2005
First published
24 May 2005

Org. Biomol. Chem., 2005,3, 2410-2419
Article type
Paper

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

I. Paterson, M. J. Coster, D. Y.-K. Chen, K. R. Gibson and D. J. Wallace, Org. Biomol. Chem., 2005, 3, 2410
DOI: 10.1039/B504148A

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