Highly stereocontrolled total synthesis of leukotriene B4, 20-hydroxyleukotriene B4, leukotriene B3, and their analogs

Y Kobayashi, T Shimazaki, H Taguchi…

Index: Kobayashi, Yuichi; Shimazaki, Toshiyuki; Taguchi, Hideki; Sato, Fumie Journal of Organic Chemistry, 1990 , vol. 55, # 19 p. 5324 - 5335

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Citation Number: 74

Abstract

A highly stereocontrolled and practical new method for synthesis of LTB,(l), 20-OH-LTB4 (2), and LTBB (3) has been developed, which uses the palladium-catalyzed coupling reaction of the vinylborane 5, derived from the C (l)-C (9) fragment 4, with the corresponding C (lO)-C (20) fragments 6a-c. The acetylene 4 was synthesized by palladium-copper-catalyzed coupling reaction of (trimethylsily1) acetylene with the bromide 12, which was prepared ...