207991-40-0Relevant academic research and scientific papers
A Catalytic Asymmetric Synthesis of 11-Deoxy-PGF1α Using ALB, a Heterobimetallic Multifunctional Asymmetric Complex
Yamada, Ken-Ichi,Arai, Takayoshi,Sasai, Hiroaki,Shibasaki, Masakatsu
, p. 3666 - 3672 (2007/10/03)
A catalytic asymmetric synthesis of 11-deoxy-PGF1α has been achieved using a cascade Michaelaldol reaction as a key step. This cascade reaction was efficiently promoted by a catalytic use of AlLibis[(S)-binaphthoxide] complex (ALB) to give the three-component coupling product at room temperature in 92percent ee and in 84percent yield. The three-component coupling product was then converted to (+)-ll-deoxy-PGF1α through several steps, including an oxidative decarboxylation, an aldol reaction, and a Wharton reaction. Moreover, the racemic enone, 20 was transformed into 21, the three-component coupling product, a potential intermediate for PGF1α in 97percent ee and in 75percent yield through catalytic kinetic resolution.
