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Towards the Total Synthesis of Spirovibsanin A: Total Synthesis of (±)‐5,14‐Bis‐ epi ‐spirovibsanin A
Author(s) -
Gallen Michael J.,
Williams Craig M.
Publication year - 2008
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.200800574
Subject(s) - total synthesis , chemistry , diterpene , derivative (finance) , stereochemistry , organic chemistry , economics , financial economics
Studies towards the total synthesis of the complex diterpene spirovibsanin A are herein presented, which culminate in an 18‐step total synthesis. Considering the perceived stereochemical uncertainty surrounding the assignment of spirovibsanin A these studies have allowed a direct spectroscopic comparison of the (±)‐5,14‐bis‐ epi derivative to that of natural spirovibsanin A demonstrating that the carbon framework and stereochemistry assigned to natural spirovibsanin A is most likely correct.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)