期刊
HELVETICA CHIMICA ACTA
卷 104, 期 12, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/hlca.202100170
关键词
catalysis; catalytic crotylboration; cross-coupling; enantioselectivity; metathesis; natural products
资金
- Czech Science Foundation [2129124S]
A general modular enantioselective synthetic approach was developed for the C(7)-C(18) and the C(7)-C(20) fragments belonging to E-492, actinofuranone A, and JBIR-108. The key step involves highly enantioselective crotylboration of aldehydes catalyzed by a chiral TRIP PA, leading to highly enantioenriched terminal alkenes. Followed by additional synthetic steps including Ru-catalyzed alkene cross-metathesis and Suzuki coupling reactions, the approach starts from easily available aldehydes and other reaction partners.
A general modular enantioselective synthetic approach to the C(7)-C(18) and the C(7)-C(20) fragment belonging to E-492, actinofuranone A, and JBIR-108 was developed. The crucial synthetic step relies on highly enantioselective crotylboration of aldehydes catalyzed by a chiral TRIP PA giving rise to highly enantioenriched terminal alkenes (86 and 88 % ee on the preparative scale). The alkenes were subsequently converted into the title products. Further important synthetic steps included Ru-catalyzed alkene cross-metathesis and Suzuki coupling reactions. The approach consists of five synthetic steps starting from easily available aldehydes and other reaction partners.
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