- 作者: 成公明 ; Yang, Jun
- 作者服務機構: Dept. of Chemistry, The Chinese Univ. of Hong Kong, Shatin, Hong Kong
- 中文摘要: The absolute configuration of natural oblongolide is reassigned as (3aS,5aR,7S,9aS,9bS)-3a,5a,6,7,8,9,9a,9b- octahydro-7,9b-dimethylnaphtho [ 1,2-c ] furan-1(3H)-one by a 7-stage synthesis of its enantiomer from (+)-citronellol involving a regioselective reduction and an intramolecular Diels-Alder reaction (IMDA) as the key steps. (+)- Citronellol was converted into methyl (2E,4E,10E)-(S)-(+)- 11-tert-butoxycarbonyl-7-methyl-undeca-2,4,10-trienoate (7) by sequential Lemieux-Johnson oxidation, Wittig reaction, pyridinium chlorochromate oxidation, and Wadsworth-Emmons- Horner alkenation. A regioselective reduction of the methoxycarbonyl group in (7) afforded tert-butyl (2E,8E,10E)-(S)-(+)-2,6-dimethyl-12-hydroxy-dodeca-2,8,10- trienoate from which (+)-oblongolide was readily obtained via an IMDA reaction.
- 英文摘要: --
- 中文關鍵字: Absolute Configuration; Citronellol; Intramolecular Diels-Alder Reaction; Wittig Reaction; Oblongolide
- 英文關鍵字: 絕對形狀;香茅醇;分子間Diels-Alder反應;Wittig反應