Formal synthesis of cis-solamin: acid-catalyzed one-step construction of 2, 5-disubstituted tetrahydrofuran. Issue 16 (10th April 2018)

• Record Type: Journal Article
• Authors: Ota, Koichiro; Yamashita, Tomoko; Kohno, Sumika; Miura, Atsuko; Kamaike, Kazuo; Miyaoka, Hiroaki
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 16(2018)
• Page Start: 3018
• Page End: 3025
• Publication Date: 2018-04-10
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob00603b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A concise and stereoselective synthesis of a 2, 5-disubstituted tetrahydrofuran was developed and applied to the formal synthesis of cis -solamin. Abstract : A divergent strategy has been used for the concise and efficient enantioselective formal synthesis of Annonaceous acetogenin cis -solamin. Our synthetic strategy comprises concise preparation of the diepoxyester via an 11-membered silaketal constructed by ring-closing metathesis after the dimerization of chiral epoxides, and uses an acid-catalyzed tandem intramolecular SN 2-like reaction to construct the threo-cis-threo configuration of the tetrahydrofuran-diol moiety.