Efficient Total Synthesis of Lycophyll (ψ, ψ-Carotene-16, 16'-diol)

…, GT Nadolski, C Braun, SF Lockwood

Index: Jackson, Henry L.; Nadolski, Geoffry T.; Braun, Cristi; Lockwood, Samuel F. Organic Process Research and Development, 2005 , vol. 9, # 6 p. 830 - 836

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Citation Number: 8

Abstract

A practical procedure is described for the total synthesis of lycophyll (16, 16'-dihydroxy- lycopene; ψ, ψ-carotene-16, 16'-diol), based on a C10+ C20+ C10 synthetic methodology using the commercially available materials geraniol (C10) and crocetindialdehyde (C20). A late-stage double Wittig olefination on crocetindialdehyde was used to form the desired lycophyll scaffold in eight linear synthetic steps, while generating a mixture of polyenic ...