Asymmetric synthesis of isohaliclorensin,a key intermediate of bisquinolinylpyrrole alkaloid halitulin |
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| Institution: | 1. Department of Otolaryngology - Head and Neck Surgery, Beilinson Campus, Petah Tiqwa, Israel;2. Department of Pathology, Rabin Medical Center, Beilinson Campus, Petah Tiqwa, Israel;3. Felsenstein Research Medical Center, Beilinson Campus, Petah Tiqwa, Israel;4. Sackler School of Medicine, Tel Aviv University, Tel Aviv, Israel |
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| Abstract: | A new enantioselective total synthesis of N-(3′-aminopropyl)-3-methylazacyclodecane, a partial structure of halitulin, has been achieved in eight steps with 14% overall yield. The key steps are the photochemical ring-expansion reaction of spirooxaziridine to lactam for constructing the azacyclodecane moiety and 1,4-stereoinductive methylation of the resulting lactam. |
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