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. 1970 Nov;67(3):1465-7.
doi: 10.1073/pnas.67.3.1465.

Application of the chloro ketal Claisen reaction to the total synthesis of squalene

L Werthemann, W S Johnson

Application of the chloro ketal Claisen reaction to the total synthesis of squalene

L Werthemann et al. Proc Natl Acad Sci U S A. 1970 Nov.

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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References

    1. Proc Natl Acad Sci U S A. 1970 Nov;67(3):1462-4 - PubMed

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