Systematic construction of a monotetrahydrofuran-ring library in annonaceous acetogenins by asymmetric alkynylation and stereodivergent tetrahydrofuran-ring formation |
| |
Authors: | Kojima Naoto Maezaki Naoyoshi Tominaga Hiroaki Asai Mikito Yanai Minori Tanaka Tetsuaki |
| |
Institution: | Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan. |
| |
Abstract: | All eight diastereoisomers of the monotetrahydrofuran-ring cores of annonaceous acetogenins have been synthesized through utilization of asymmetric alkynylation and stereodivergent one-pot tetrahydrofuran-ring formation. In all cases, the asymmetric alkynylation proceeded with very high diastereoselectivity to give eight kinds of optically pure tetrahydrofuran core from a common alpha-oxyaldehyde. We also describe a comparison of the (1)H NMR, (13)C NMR, and CD spectral data of the eight isomers and give full details of the tetrahydrofuran-ring construction including a model study of asymmetric alkynylation. |
| |
Keywords: | alkynylations cyclization polyketides stereodivergent synthesis synthetic methods |
本文献已被 PubMed 等数据库收录! |
|