A Total Synthesis of (+)-Hirsutic Acid

• Published in: Chemical & pharmaceutical bulletin Vol. 38; no. 12; pp. 3230 - 3237
• Main Authors: IKEGAMI, Shiro, NISHIDA, Mayumi, ISEKI, Katsuhiko, SHIBASAKI, Masakatsu
• Format: Journal Article
• Language: English
• Published: Tokyo The Pharmaceutical Society of Japan 1990; 公益社団法人日本薬学会; Maruzen; Japan Science and Technology Agency
• Subjects: (+)-2-cyclopenteneacetic acid; (+)-di-3-pinanylborane; asymmetric synthesis; chelation-controlled reaction; Chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Organic chemistry; potassium pyrosulfate; Preparations and properties; Simmons-Smith reaction; Wacker-type oxidation; Enantiomer(+); Asymmetric synthesis; Carboxylic acid; Epoxide; Tetracyclic compound; Secondary alcohol; Antibacterial agent; Oxygen heterocycle; Ethylenic compound; Total synthesis
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.38.3230

The first asymmetric total synthesis of (+)-hirsutic acid has been accomplished in a highly stereocontrolled manner, including a novel method for the preparation of (1S, 5R, 6S)-6-hydroxy-cis-bicyclo[3.3.0]octan-3-one and a stereospecific Simmons-Smith reaction controlled by the participation of a relatively remote hydroxyl group.