Premium
Enantioselective Total Synthesis of Brevetoxin A: Convergent Coupling Strategy and Completion
Author(s) -
Crimmins Michael T.,
Zuccarello J. Lucas,
McDougall Patrick J.,
Ellis J. Michael
Publication year - 2009
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.200900777
Subject(s) - enantioselective synthesis , convergent synthesis , total synthesis , ether , chemistry , wittig reaction , oxidative phosphorylation , natural product , organic chemistry , stereochemistry , combinatorial chemistry , catalysis , biochemistry
A highly convergent, enantioselective total synthesis of brevetoxin A is reported. The development of a [X+2+X] Horner–Wadsworth–Emmons/cyclodehydration/reductive etherification convergent coupling strategy allowed a unified approach to the synthesis of two advanced tetracyclic fragments from four cyclic ether subunits. The Horner–Wittig coupling of the two tetracyclic fragments provided substrates that were explored for reductive etherification, the success of which delivered a late‐stage tetraol intermediate. The tetraol was converted to the natural product through an expeditious selective oxidative process followed by methylenation.