Synthesis of (all‐ E ,2 R ,2′ R )‐oscillol | Zendy

Traber Bruno | Zendy; Pfander Hanspeter | Zendy

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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

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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