Total Syntheses of the Tetracyclic Cyclopiane Diterpenes Conidiogenone,Conidiogenol, and Conidiogenone B |
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| Authors: | Dr. Si‐Hua Hou Prof. Dr. Yong‐Qiang Tu Shuang‐Hu Wang Chao‐Chao Xi Prof. Dr. Fu‐Min Zhang Prof. Dr. Shao‐Hua Wang Yan‐Tao Li Lin Liu |
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| Affiliation: | 1. State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, P.R. China;2. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, P.R. China;3. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, P.R. China |
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| Abstract: | Total syntheses of the biologically important and structurally unique tetracyclic diterpenes conidiogenone, conidiogenol, and conidiogenone B of the cyclopiane class are reported. The absolute configuration of naturally occurring conidiogenone B was also corrected. The key step of our strategy involved the highly efficient construction of both ring C and the quaternary carbon center shared by rings A and C through a one‐step regioselective and diastereoselective cycloenlargement in the form of a semipinacol‐type rearrangement. In particular, the desired regioselectivity was made possible by properly adjusting the migratory aptitude of the migrating carbon atom through the introduction of an electron‐donating phenylthio group at this position. |
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| Keywords: | cyclization natural products semipinacol rearrangement tetracyclic diterpenes total synthesis |
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