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Synthesis of (all-E,2R,2′R)-oscillol

✍ Scribed by Bruno Traber; Hanspeter Pfander

Publisher
John Wiley and Sons
Year
1996
Tongue
German
Weight
472 KB
Volume
79
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Optically active (all‐E,2__R__,2′R)‐oscillol (= (all‐E,2__R__,2′R)‐3,4,3′,4′‐tetradehydro‐1,2,1′,2′‐tetrahydro‐ψ,ψ‐carotene‐1,2,1′,2′‐tetrol; 1) was synthesized according to the C~10~ + C~20~ + C~10~ = C~40~ strategy, applying the Wittig reaction to couple the synthons 4 and 6. The chiral centre was introduced by a Sharpless dihydroxylation of 3‐methylbut‐2‐enyl 4‐nitrobenzoate (8).

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