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. 1970 Nov;67(3):1465–1467. doi: 10.1073/pnas.67.3.1465

Application of the Chloro Ketal Claisen Reaction to the Total Synthesis of Squalene*

Lucius Werthemann 1, William S Johnson 1
PMCID: PMC283375  PMID: 5274470

Abstract

A short, highly stereoselective (over 97%) synthesis of all-trans squalene is described. Starting with succinaldehyde, a tetraenedichlorodione having the complete squalene skeleton with the four internal trans olefinic bonds has been developed in four steps involving a sequence of two double Claisen rearrangements. Three simple operations convert this intermediate into squalene.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Loew P., Siddall J. B., Spain V. L., Werthemann L. A short stereoselective synthesis of cecropia juvenile hormone. Proc Natl Acad Sci U S A. 1970 Nov;67(3):1462–1464. doi: 10.1073/pnas.67.3.1462. [DOI] [PMC free article] [PubMed] [Google Scholar]

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