Diastereoselective Synthesis of the A‐B‐C Tricyclic Ring Structure of Stemocurtisine. Issue 35 (9th November 2015)

• Record Type: Journal Article
• Authors: Dau, Xuan Duc; Willis, Anthony C.; Pyne, Stephen G.
• Is Part Of: European journal of organic chemistry. Issue 35(2015)
• Page Start: 7682
• Page End: 7694
• Publication Date: 2015-11-09
• Subjects: Natural products -- Alkaloids -- Nitrogen heterocycles -- Diastereoselectivity -- Cyclization -- Epoxidation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201501080
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The diastereoselective synthesis of the A‐B‐C tricyclic ring structure of the Stemona alkaloid stemocurtisine is described. This tricyclic precursor to the natural product was obtained in 19 steps from a known vinyl iodide. Attempts to prepare the C‐3a–C‐11 ether moiety of this alkaloid through a photochemically induced oxidative cyclization method were unsuccessful because of the cleavage of the A‐ring. Abstract : The diastereoselective synthesis of the A‐B‐C tricyclic ring structure of the Stemona alkaloid stemocurtisine has been developed. This tricyclic precursor to the natural product was obtained in 19 steps from a known vinyl iodide (TBS = tert ‐butyldimethylsilyl).