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Total Synthesis of Gambierol: The Generation of the A–C and F–H Subunits by Using a C‐Glycoside Centered Strategy
Author(s) -
Majumder Utpal,
Cox Jason M.,
Johnson Henry W. B.,
Rainier Jon D.
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200500993
Subject(s) - stereochemistry , stereocenter , chemistry , olefin fiber , enol , ether , enol ether , vinyl ether , organic chemistry , enantioselective synthesis , catalysis , polymer , copolymer
Gambierol, a representative of the marine ladder toxin family, consists of eight ether rings, 18 stereocenters, and two challenging pyranyl rings having methyl groups that are in a 1,3‐diaxial orientation to one another. Herein we describe the generation of gambierol's A–C and F–H ring systems and demonstrate the versatility of the glycosyl anhydride, enol ether–olefin RCM strategy to fused polycyclic ethers. This work has both enabled us to generate sufficient quantities of the gambierol precursors and has enabled us to better understand the chemical transformations that were key to these efforts. Fundamental work included efforts to C‐glycosides and C‐ketosides, Claisen rearrangements, and enol ether–olefin RCM reactions.