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

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.

authors

Werthemann L,Johnson WS

doi

10.1073/pnas.67.3.1465

subject

Has Abstract

pub_date

1970-11-01 00:00:00

pages

1465-7

issue

3

eissn

0027-8424

issn

1091-6490

journal_volume

67

pub_type

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