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A Catalytic Asymmetric Synthesis of 11-Deoxy-PGF 1α Using ALB, a Heterobimetallic Multifunctional Asymmetric Complex

1998; American Chemical Society; Volume: 63; Issue: 11 Linguagem: Inglês

10.1021/jo9723319

1520-6904

Ken‐ichi Yamada, Takayoshi Arai, Hiroaki Sasai, Masakatsu Shibasaki,

Catalytic C–H Functionalization Methods

A catalytic asymmetric synthesis of 11-deoxy-PGF1α has been achieved using a cascade Michael−aldol 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 92% ee and in 84% yield. The three-component coupling product was then converted to (+)-11-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 97% ee and in 75% yield through catalytic kinetic resolution.