Synthesis of 10, 11-dihydroleukotriene B4 metabolites via a nickel-catalyzed coupling reaction of cis-bromides and trans-alkenyl borates

Y Nakayama, GB Kumar…

Index: Nakayama, Yuji; Kumar, G. Biju; Kobayashi, Yuichi Journal of Organic Chemistry, 2000 ,  vol. 65,  # 3  p. 707 - 715

Full Text: HTML

Citation Number: 31

Abstract

Synthesis of 10, 11-dihydro-, 10, 11, 14, 15-tetrahydro-, and 10, 11-dihydro-12- oxoleukotriene B4 compounds (2, 4, 5) was accomplished stereoselectively by using the nickel-catalyzed coupling reaction illustrated in Scheme 1. The C (1)-C (7) fragments, TBS ether 10a for 2 and 4 and ethyoxyethyl (EE) ether 10b for 5, were prepared in enantiomerically pure forms (> 99% ee) by a modified literature procedure (ref 11a). On ...