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Total Synthesis of (−)‐Haouamine B Pentaacetate and Structural Revision of Haouamine B |
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| Authors: | Yuichi Momoi Dr. Kei‐ichiro Okuyama Dr. Hiroki Toya Dr. Kenji Sugimoto Dr. Kentaro Okano Prof. Dr. Hidetoshi Tokuyama |
| Affiliation: | Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Aramaki, Aoba‐ku, Sendai 980‐8578 (Japan) |
| Abstract: | The enantiocontrolled total synthesis of (?)‐haouamine B pentaacetate was accomplished via an optically active indane‐fused β‐lactam, which was prepared by a newly developed Friedel–Crafts reaction. Subsequent cleavage of the β‐lactam and an intramolecular McMurry coupling reaction provided the core indane‐fused tetrahydropyridine, which led to the elucidation of the structure, as proposed by Trauner and Zubía. |
| Keywords: | alkaloids aromatic substitution cross‐coupling cyclization total synthesis |