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Total Synthesis of (–)‐Neovibsanin G and (–)‐14‐ epi ‐Neovibsanin G: Towards the Synthesis of 15‐ O ‐Methylneovibsanin F and 14‐ epi ‐15‐ O ‐Methylneovibsanin F
Author(s) -
Mak Jeffrey Y. W.,
Williams Craig M.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101796
Subject(s) - chemistry , total synthesis , stereochemistry , methanol , biosynthesis , organic chemistry , enzyme
The total synthesis of (–)‐neovibsanin G and (–)‐14‐ epi ‐neovibsanin G has been accomplished, establishing the absolute configurations of these caged diterpenes as 11 S , and confirming Fukuyama's postulated biosynthesis of the neovibsanins. Synthetic studies towards 15‐ O ‐methylneovibsanin F and 14‐ epi ‐15‐ O ‐methylneovibsanin F were undertaken based on the hypothesis that these methoxy substituted caged neovibsanins were artifacts of isolation, formed by the addition of methanol to the terminal alkenes of neovibsanin G and 14‐ epi ‐neovibsanin G. The results strongly suggest, however, that the methoxy caged neovibsanins are true natural products.