Preparation of Divergent Intermediates and Convergent Synthesis of Phytofluene

This paper is dedicated to the late Prof. Synnøve Liaaen-Jensen for her dedication to carotenoid research.

Abstract

Practical synthetic methods for biogenetically and pharmaceutically important phytofluene were developed through the divergent preparation of key C₂₀ substrates from a common intermediate and convergent synthesis by Wittig and Julia–Kocienski olefinations. Expeditious synthesis of phytofluene was also proposed based on the Julia sulfone-mediated chain-extension and double elimination method. Stereochemical outcomes of these olefination methods for phytofluene were compared and the Julia–Kocienski method was the mildest and most efficient reaction condition to produce all-(E)-phytofluene. Complete ¹H and ¹³C NMR analysis of all-(E)-phytofluene is reported for the first time. Phytofluene undergoes facile thermal isomerization to other Z-isomers above room temperature, which was also confirmed with a C₃₀ phytofluene homologue.

Key words

carotenoids - isomerization - olefination - phytofluene - sulfones - total synthesis

Publication History

Received: 17 February 2023

Accepted after revision: 15 March 2023

Accepted Manuscript online:
15 March 2023

Article published online:
19 April 2023

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