Chemical modification of paraherquamide. 1. Unusual reactions and absolute stereochemistry

…, H Mrozik, MH Fisher, K Hoogsteen…

Index: Blizzard, Timothy A.; Marino, Gaye; Mrozik, Helmut; Fisher, Michael H.; Hoogsteen, Karst; Springer, James P. Journal of Organic Chemistry, 1989 , vol. 54, # 11 p. 2657 - 2663

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Citation Number: 29

Abstract

The reaction of paraherquamide (1) with phosgene to form a rearranged cyclic urethane (3) is reported. An unusual Super-Hydride-mediated reductive cyclization of 3 to the interesting analogues 4, 5, and 6 is also described. Conversion of chloride 3 to the corresponding alcohol 12 is discussed. The absolute stereochemistry of 1 is determined by single-crystal X- ray analysis of a brominated derivative of 12. In addition, several other paraherquamide ...