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2,6-Cyclolycopene-1,5-diol: Total synthesis of a naturally occurring oxidation product of lycopene

✍ Scribed by Bruno Traber; Hanspeter Pfander

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
624 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

2,6-Cyclolycopene-l,5-diol (3) was synthesized in 9 steps starting from ¢t-terpinyl acetate (11). This represents the first total synthesis of an oxidative metabolite of lycopene (2). The synthesis was performed according to a C~.s + C~o + Cm5 = C40 strategy using the Wittig olefination to couple the end groups to the central building block. An intramolecular aldol addition was used to introduce two new stereocenters with a defined relative stereochemistry.

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