A biomimetic total synthesis of (+)-intricarene |
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Authors: | Bencan Tang |
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Institution: | School of Chemistry, The University of Nottingham, Nottingham NG7 2RD, UK |
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Abstract: | An asymmetric synthesis of the furanocembrane (−)-bipinnatin J (3a) found in gorgonian corals is described. Treatment of 3a with VO(acac)2-tBuOOH, followed by acetylation, gave acetoxypyranone 15. When 15 was heated in the presence of DBU, it underwent a transannular oxidopyrylium-alkene 5+2] cycloaddition producing the polycyclic diterpene (+)-intricarene 1, isolated from the coral Pseudopterogorgia kallos. The total synthesis of intricarene 1 mimics its most likely biosynthesis via oxidation of bipinnatin J (3a) in vivo. |
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