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Total synthesis of (−)-physovenine from (−)-3a-hydroxyfuroindoline |
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| Authors: | Toshiaki Sunazuka Kiminari Yoshida Tatsuya Shirahata Masaki Handa Yoshihiro Harigaya Satoshi ōmura |
| Affiliation: | a Kitasato Institute for Life Sciences, Kitasato University and CREST, Shirokane, Minato-ku, Tokyo 108-8641, Japan b School of Pharmaceutical Sciences, Kitasato University, Shirokane, Minato-ku, Tokyo 108-8641, Japan c The Kitasato Institute, Shirokane, Minato-ku, Tokyo 108-8642, Japan |
| Abstract: | Total synthesis of calabar bean alkaloid (−)-physovenine (−)-3 has been achieved in a concise manner starting from optically active (−)-3a-hydroxyfuroindoline (−)-2, synthesized via modified Sharpless epoxidation of tryptophol 1. Our strategy involved a stereospecific radical substitution reaction and regioselective oxidation at the C5 position. |
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