2. Academic Validation
  3. Total synthesis of cochleamycin A

Total synthesis of cochleamycin A

  • Org Lett. 2004 Jun 10;6(12):2043-6. doi: 10.1021/ol049331x.
Thomas A Dineen 1,  William R Roush
Affiliations

Affiliation

  • 1 Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
PMID: 15176814 DOI: 10.1021/ol049331x
Abstract

[reaction: see text] Cochleamycin A (1) was synthesized in 2.4% overall yield via a 23-step linear sequence starting from 3-butene-1-ol. Key features of the synthesis include the synthesis of (Z)-1,3-diene 21 via a Stille coupling of 4 and 5 and a transannular Diels-Alder reaction of macrocycle 26 to provide the complete carbon skeleton of 1.

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