Premium
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom