Total Synthesis of (−)‐Enigmazole A |
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| Authors: | Keisuke Sakurai Prof?Dr Makoto Sasaki Prof?Dr Haruhiko Fuwa |
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| Institution: | 1. Graduate School of Life Sciences, Tohoku University, Aoba-ku, Sendai, Japan;2. Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Tokyo, Japan |
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| Abstract: | Total synthesis of (?)‐enigmazole A, a marine macrolide natural product with cytotoxic activity, has been accomplished. The tetrahydropyran moiety was constructed by means of a domino olefin cross‐metathesis/intramolecular oxa‐Michael addition of a δ‐hydroxy olefin. After coupling of advanced intermediates, the macrocycle was formed through gold‐catalyzed rearrangement of a propargylic benzoate, followed by ring‐closing metathesis of the resultant α,β‐unsaturated ketone. |
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| Keywords: | macrocycles metathesis natural products rearrangement total synthesis |
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