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Synthesis of 6-(poly)prenyl-substituted polyprenols and their phosphates

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
55
Issue
9
Identifiers
DOI: 10.1016/s0040-4020(99)00057-5

Abstract

Abstract The 6-(poly)prenyl-substituted polyprenols 7, 9, 11, and 13 were synthesized: (1) 7 from 2-geranyl-farnesal and methyl 4-bromo-3-methyl-2-butenoate, (2) 9 from 2-prenyl-geranyl bromide and ethyl acetoacetate, via ketone 29, (3) 11 from ethyl acetoacetate, geranyl bromide, and ( E)-1- t-butyldiphenylsiloxy-5-iodo-3-methyl-2-pentene, via β-keto ester 35, and (4) 13 from geraniol by acid catalyzed condensation. These highly branched polyprenols 7, 9, 11, and 13 were transformed into the corresponding disodium phosphates 8, 10, 12, and 14, respectively.

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