Stereodivergent and reiterative synthesis of bistetrahydrofuran ring cores of annonaceous acetogenins |
| |
Authors: | Kojima Naoto Maezaki Naoyoshi Tominaga Hiroaki Yanai Minori Urabe Daisuke Tanaka Tetsuaki |
| |
Affiliation: | Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan. |
| |
Abstract: | Eight diastereoisomers of the bistetrahydrofuran ring cores of annonaceous acetogenins have been synthesized by asymmetric alkynylation of alpha-tetrahydrofuranic aldehydes and stereodivergent one-pot tetrahydrofuran (THF) ring formation. In all cases, the asymmetric alkynylation proceeded with very high diastereoselectivity to give eight kinds of optically pure THF cores. We also describe a comparison of the (1)H and (13)C NMR spectral data of the eight isomers and give full details of the THF ring construction. |
| |
Keywords: | annonaceous acetogenins asymmetric alkynylation cyclization stereodivergent synthesis synthetic methods |
本文献已被 PubMed 等数据库收录! |