Synthesis of (+)-Strigol and (+)-Orobanchol, the Germination Stimulants, and Their Stereoisomers by Employing Lipase-Catalyzed Asymmetric Acetylationas the Key Step

✍ Scribed by Kouichi Hirayama; Kenji Mori

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 241 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199909)1999:9<2211::aid-ejoc2211>3.0.co;2-o

✦ Synopsis

The potent seed germination stimulants (+)-strigol (1), (+)-2Ј-bisepiorobanchol (2ЈЈЈ)] were prepared from the enantiomers of 3, which were obtainable by lipase-catalyzed orobanchol (2) and their stereoisomers [2Ј-epistrigol (1Ј), ent-1, ent-1Ј, 2Ј-epiorobanchol (2Ј), 4-epiorobanchol (2ЈЈ) and 4, enantiomer separation of (±)-3.

Scheme 1. Structures of strigol and related compounds [ ] Part 4: Ref. [11] [a] Department of Chemistry, tive synthesis. The practical way to obtain (ϩ)-1 must there-Faculty of Science, Science University of Tokyo, fore depend on enantiomer separation of (±)-1 or one of its Kagurazaka 1Ϫ3,