Total syntheses of (+)-zampanolide and (+)-dactylolide exploiting a unified strategy.

Abstract

The first total syntheses of (+)-zampanolide (1) and (+)-dactylolide (2), members of a new class of tumor cell growth inhibitory macrolides, have been achieved. Key features of the unified synthetic scheme included the stereocontrolled construction of the cis-2,6-disubstituted tetrahydropyran via a modified Petasis-Ferrier rearrangement, a highly convergent assembly of the macrocyclic domain, and, in the case of zampanolide, a Curtius rearrangement/acylation tactic to install the N-acyl hemiaminal. The complete relative and absolute stereochemistries for both (+)-zampanolide and (+)-dactylolide were also assigned, albeit tentatively in the case of (+)-zampanolide (1).

• Authors: Amos B Smith 3rd, Igor G Safonov, R Michael Corbett
• Journal: Journal of the American Chemical Society (J Am Chem Soc) Vol. 124 Issue 37 Pg. 11102-13 (Sep 18 2002) ISSN: 0002-7863 [Print] United States
• PMID: 12224958 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, P.H.S.)

Chemical References

• Antineoplastic Agents
• Bridged Bicyclo Compounds, Heterocyclic
• Lactones
• Macrolides
• dactylolide
• zampanolide

Topics

• Animals
• Antineoplastic Agents (chemical synthesis)
• Bridged Bicyclo Compounds, Heterocyclic (chemical synthesis)
• Lactones (chemical synthesis)
• Macrolides (chemical synthesis)
• Molecular Conformation
• Porifera (chemistry)
• Stereoisomerism