Highly stereoselective and stereodivergent synthesis of four types of THF cores in acetogenins using a C4-chiral building block |
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Authors: | Maezaki Naoyoshi Kojima Naoto Asai Mikito Tominaga Hiroaki Tanaka Tetsuaki |
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Institution: | Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan. |
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Abstract: | reaction: see text] Four stereoisomers of the THF cores, synthetic intermediates of acetogenins, have been synthesized with high diastereoselectivity by asymmetric alkynylation and subsequent stereodivergent THF ring formation. The asymmetric alkynylation of alpha-oxyaldehyde with (S)-3-butyne-1,2-diol derivatives (C4-unit) gave good yields of syn and anti adducts with >97:3 dr and 94:6 dr, respectively. These adducts were converted into the four types of THF compounds via one-pot THF formation or via intramolecular Williamson synthesis. |
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