Total Synthesis of (±)-Methyl Rishirilide B

• Published in: Organic letters Vol. 1; no. 2; pp. 335 - 336
• Main Authors: Hauser, Frank M, Xu, Yong-jin
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 29.07.1999; Amer Chemical Soc
• Subjects: alpha-Macroglobulins - antagonists & inhibitors; Anthracenes - chemical synthesis; Anthracenes - chemistry; Chemistry; Chemistry, Organic; Fibrinolytic Agents - chemical synthesis; Hydrolysis; Indicators and Reagents; Physical Sciences; Science & Technology; Stereoisomerism; Streptomyces - chemistry
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol9906561

A regio- and stereospecific total synthesis of (±)-methyl rishirilide B (2b), an (α)2-macroglobulin inhibitor, is described. A key feature of the synthetic plan was regiospecific construction of a hydroanthracenone intermediate through condensation of a phenylsulfonyl isobenzofuranone with a functionalized 2-cyclohexen-1-one. Introduction of the vicinal trans-hydroxyl groups in the densely functionalized A-ring was accomplished via a novel one-pot procedure that involved oxidation of enolate anions with the Davis reagent.