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Synthesis of Allylic Isoprenoid Diphosphates by SN2 Displacement of Diethyl Phosphate

✍ Scribed by Matthew M. Ravn; Qingwu Jin; Robert M. Coates

Publisher
John Wiley and Sons
Year
2000
Tongue
English
Weight
344 KB
Volume
2000
Category
Article
ISSN
1434-193X

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✦ Synopsis

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 S N 2 displacements with tris(tetrabutylammonium) pyrophosphate which occurred slowly with essentially complete inversion of configuration over 2-5 days. The 8α-and 8β-hydroxy-17-nor analogs (13 and 14) of copalyl diphosphate as well as the (15R)deuterium-labeled form of 13 were similarly prepared from

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