Enantioselective strategy to the spirocyclic core of Palau'amine and related bisguanidine marine alkaloids.
[structure: see text] An enantioselective strategy to the spirocyclic core found in the oroidin-derived family of bisguanidine marine alkaloids has been devised, premised on a biosynthetic proposal. Herein, we describe the successful implementation of this strategy, which entails a Diels-Alder reaction and a chlorination/ring contraction sequence that delivers the fully functionalized spirocyclic core. In this initial report, an intermolecular chlorination delivers a cyclopentane that is epimeric at C17 relative to the palau'amines and epimeric at C11 relative to the axinellamines.
Dilley
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AS
Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, Texas 77843-3012, USA.
Romo
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D
D000470:Alkaloids / Q000138:chemical synthesis*; D000588:Amines / Q000138:chemical synthesis; D006146:Guanidines / Q000138:chemical synthesis*; D007166:Immunosuppressive Agents / Q000138:chemical synthesis*; D008386:Marine Biology; D013141:Spiro Compounds / Q000138:chemical synthesis; D013237:Stereoisomerism
D000470:Alkaloids; D000588:Amines; D006146:Guanidines; D007166:Immunosuppressive Agents; D013141:Spiro Compounds; C438977:batzelladine A