Stereoselective synthesis of premisakinolide A, the monomeric counterpart of the marine 40-membered dimeric macrolide misakinolide A.

Abstract

[structure: see text] The first synthesis of premisakinolide A, the monomeric counterpart of misakinolide A, the marine 40-membered macrolide displaying potent activity against a variety of human carcinoma cell lines, has been reported. The strategy was highlighted by a crucial coupling of a tetrahydropyran fragment and an alkynylaluminum reagent having a polypropionate chain, the highly stereoselective cross aldol reaction of segment A and segment B, and the stereospecific construction of the polypropionate structure based on original acyclic stereocontrol.

• Authors: Ryoichi Nakamura, Keiji Tanino, Masaaki Miyashita
• Journal: Organic letters (Org Lett) Vol. 7 Issue 14 Pg. 2929-32 (Jul 07 2005) ISSN: 1523-7060 [Print] United States
• PMID: 15987172 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Macrolides
• premisakinolide A
• bistheonellide A

Topics

• Animals
• Drug Screening Assays, Antitumor
• Humans
• Macrolides (analysis, chemical synthesis, chemistry, pharmacology)
• Marine Biology
• Molecular Structure
• Porifera (chemistry)
• Stereoisomerism
• Tumor Cells, Cultured