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Synthesis of (all‐ E ,2 R ,2′ R )‐oscillol
Author(s) -
Traber Bruno,
Pfander Hanspeter
Publication year - 1996
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19960790217
Subject(s) - synthon , chemistry , dihydroxylation , optically active , wittig reaction , stereochemistry , sharpless asymmetric dihydroxylation , enantioselective synthesis , organic chemistry , catalysis
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 ).