Synthesis of allylic isoprenoid diphosphates by SN2 displacement of diethyl phosphate

MM Ravn, Q Jin, RM Coates

Index: Ravn, Matthew M.; Jin, Qingwu; Coates, Robert M. European Journal of Organic Chemistry, 2000 , # 8 p. 1401 - 1410

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Citation Number: 17

Abstract

Abstract Allylic polyenyl diphosphates such as geranyl and (E, E, E)-geranylgeranyl diphosphates are ubiquitous substrates for monoterpene and diterpene synthases and transferases in isoprenoid biosynthesis. These enzyme substrates were prepared in asymmetrically labeled form by reduction of 1-deuterio aldehyde precursors with (R)-and (S)- Alpine boranes®, conversion into diethyl phosphates, and SN 2 displacements with tris ( ...