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Asymmetric Total Synthesis of (−)‐Indicol by a Carbene Cyclization–Cycloaddition Cascade Strategy
Author(s) -
Lam Sze Kui,
Chiu Pauline
Publication year - 2007
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.200700838
Subject(s) - stereocenter , domino , carbene , cycloaddition , cascade reaction , yield (engineering) , chemistry , cascade , rhodium , undecane , total synthesis , combinatorial chemistry , stereochemistry , medicinal chemistry , enantioselective synthesis , organic chemistry , catalysis , physics , chromatography , thermodynamics
The first total synthesis of a secodolastane, (−)‐indicol, has been accomplished. The key reaction is a rhodium(II)‐mediated carbene cyclization–cycloaddition cascade, by which the core bicyclo[5.4.0]undecane skeleton was assembled. In this one‐pot reaction, a domino series of transformations resulting in the construction of three σ bonds and three stereocenters was realized in good yield.