Formal syntheses of (±)-Asterisca-3(15),6-diene and (±)-Pentalenene using Rh(I)-catalyzed [(5+2)+1] cycloaddition |
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| Authors: | Xiaohui Fan Lian-Gang Zhuo Zhi-Xiang Yu |
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| Institution: | a State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou 730000, PR China
b Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, PR China |
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| Abstract: | Efficient formal syntheses of (±)-Asterisca-3(15),6-diene, a natural product with a bicyclo6.3.0]undecane skeleton, and (±)-Pentalenene, a natural product with a tricyclo6.3.0.04,8]undecane skeleton, have been achieved by using Rh(I)-catalyzed (5+2)+1] cycloaddition. The (5+2)+1] reaction provides an expeditious approach to reach the bicyclic cyclooctenone 4, which was quickly transformed (via hydroboration then oxidation) to diketone 14, a key advanced intermediate for the total synthesis of (±)-Asterisca-3(15),6-diene. Through further transformations, 14 was converted to diene 18, an advanced intermediate for the total synthesis of (±)-Pentalenene. |
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