Spirastrellolide Studies. Synthesis of the C(1)-C(25) Southern Hemispheres of Spirastrellolides A and B, Exploiting Anion Relay Chemistry.

Abstract

Construction of the C(1)-C(25) southern fragments of both spirastrellolide A and B are described. Highlights of the syntheses include effective use of the three component anion relay chemistry (ARC) tactic recently introduced by our laboratory, a stereoselective spirocyclization via concomitant Ferrier reaction to elaborate the BC spiroketal and use of two dithiane unions to install the A ring as well as C(22)-C(25) fragment. The synthesis proceeded with longest linear sequences of 33 and 32 steps respectively for spirastrellolide A and spirastrellolide B.

• Authors: Amos B Smith, Helmars Smits, Dae-Shik Kim
• Journal: Tetrahedron (Tetrahedron) Vol. 66 Issue 33 Pg. 6597-6605 (Aug 14 2010) ISSN: 0040-4020 [Print] England
• PMID: 20694174 (Publication Type: Journal Article)