TY - JOUR
T1 - Intramolecular biaryl coupling reaction of benzyl benzoate and phenyl benzoate derivatives, and its application to the formal synthesis of (-)-steganone
AU - Takeda, Shigemitsu
AU - Abe, Hitoshi
AU - Takeuchi, Yasuo
AU - Harayama, Takashi
N1 - Funding Information:
A part of this work was supported by the Japan Society for the Promotion of Science to H.A. (grant no. 18590005). We also thank the SC-NMR Laboratory of Okayama University for the NMR experiments.
Copyright:
Copyright 2008 Elsevier B.V., All rights reserved.
PY - 2007/1/8
Y1 - 2007/1/8
N2 - Construction of the biaryl moiety of stegane and related compounds through an intramolecular biaryl coupling reaction is described. Undesired products were obtained by the intramolecular coupling reaction of benzyl benzoates (8, 13, and 14) because of their steric and electrostatic properties, and only that of phenyl benzoates (26b and 26c) afforded the desired biaryl lactones in good yields. An asymmetric formal synthesis of the title compound has been achieved using an enantioselective lactone-opening reaction followed by a four-step conversion to the known compound.
AB - Construction of the biaryl moiety of stegane and related compounds through an intramolecular biaryl coupling reaction is described. Undesired products were obtained by the intramolecular coupling reaction of benzyl benzoates (8, 13, and 14) because of their steric and electrostatic properties, and only that of phenyl benzoates (26b and 26c) afforded the desired biaryl lactones in good yields. An asymmetric formal synthesis of the title compound has been achieved using an enantioselective lactone-opening reaction followed by a four-step conversion to the known compound.
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U2 - 10.1016/j.tet.2006.10.059
DO - 10.1016/j.tet.2006.10.059
M3 - Article
AN - SCOPUS:33751532366
SN - 0040-4020
VL - 63
SP - 396
EP - 408
JO - Tetrahedron
JF - Tetrahedron
IS - 2
ER -