Literature DB >> 5274470

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

L Werthemann, W S Johnson.   

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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Year:  1970        PMID: 5274470      PMCID: PMC283375          DOI: 10.1073/pnas.67.3.1465

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN: 0027-8424            Impact factor:   11.205


  1 in total

1.  A short stereoselective synthesis of cecropia juvenile hormone.

Authors:  P Loew; J B Siddall; V L Spain; L Werthemann
Journal:  Proc Natl Acad Sci U S A       Date:  1970-11       Impact factor: 11.205

  1 in total
  2 in total

1.  Chemistry of the Secondary Metabolites of Termites.

Authors:  Edda Gössinger
Journal:  Prog Chem Org Nat Prod       Date:  2019

2.  A short stereoselective synthesis of cecropia juvenile hormone.

Authors:  P Loew; J B Siddall; V L Spain; L Werthemann
Journal:  Proc Natl Acad Sci U S A       Date:  1970-11       Impact factor: 11.205

  2 in total

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