Total synthesis of scytophycin C. 1. Stereoselective syntheses of the C(1)-C(18) segment and the C(19)-C(31) segment.

Abstract

[structure: see text] Stereoselective total synthesis of scytophycin C, a marine 22-membered macrolide displaying potent activity against a variety of human carcinoma cell lines, has been reported in which the polypropionate structure bearing contiguous asymmetric centers was stereospecifically constructed by using new acyclic stereocontrol. This paper describes stereoselective syntheses of the C(1)-C(18) segment (Segment A) including a trans-disubstituted dihydropyran ring and the C(19)-C(31) segment (Segment B) having eight stereogenic centers.

• Authors: Ryoichi Nakamura, Keiji Tanino, Masaaki Miyashita
• Journal: Organic letters (Org Lett) Vol. 5 Issue 20 Pg. 3579-82 (Oct 02 2003) ISSN: 1523-7060 [Print] United States
• PMID: 14507177 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents
• Bridged Bicyclo Compounds, Heterocyclic
• scytophycin C

Topics

• Antineoplastic Agents (chemical synthesis)
• Bridged Bicyclo Compounds, Heterocyclic (chemical synthesis, chemistry)
• Stereoisomerism