TY - JOUR
T1 - Asymmetric total synthesis of (-)-azaspirene, a novel angiogenesis inhibitor
AU - Hayashi, Yujiro
AU - Shoji, Mitsuru
AU - Yamaguchi, Junichiro
AU - Sato, Kenji
AU - Yamaguchi, Shinpei
AU - Mukaiyama, Takasuke
AU - Sakai, Ken
AU - Asami, Yukihiro
AU - Kakeya, Hideaki
AU - Osada, Hiroyuki
PY - 2002/10/16
Y1 - 2002/10/16
N2 - The asymmetric total synthesis of (-)-azaspirene, an angiogenesis inhibitor, has been accomplished, establishing its absolute stereochemistry. The key steps are a MgBr2·OEt2-mediated, diastereoselective Mukaiyama aldol reaction, a NaH-promoted, intramolecular cyclization of an alkynylamide, and the aldol reaction of a ketone containing functionalized γ-lactam moiety without protection of tert-alcohol and amide functionalities.
AB - The asymmetric total synthesis of (-)-azaspirene, an angiogenesis inhibitor, has been accomplished, establishing its absolute stereochemistry. The key steps are a MgBr2·OEt2-mediated, diastereoselective Mukaiyama aldol reaction, a NaH-promoted, intramolecular cyclization of an alkynylamide, and the aldol reaction of a ketone containing functionalized γ-lactam moiety without protection of tert-alcohol and amide functionalities.
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U2 - 10.1021/ja0276826
DO - 10.1021/ja0276826
M3 - Article
AN - SCOPUS:0037120884
SN - 0002-7863
VL - 124
SP - 12078
EP - 12079
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 41
ER -