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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.

SUBMITTER: Smith AB

PROVIDER: S-EPMC2915457 | biostudies-other | 2010 Aug

REPOSITORIES: biostudies-other

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

Smith Amos B AB Smits Helmars H Kim Dae-Shik DS

Tetrahedron 20100801 33

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 ste ...[more]

PMID: 20694174

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