Etudes stéréochimiques VII  Synthèses diéniques en série résinique; action des peroxoacides et des hydrures doubles | Zendy

Gastambide Bernard | Zendy; Langlois Nicole | Zendy

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Etudes stéréochimiques VII Synthèses diéniques en série résinique; action des peroxoacides et des hydrures doubles

Author(s) -

Gastambide Bernard,

Langlois Nicole

Publication year - 1968

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.19680510824

Subject(s) - chemistry , sodium borohydride , epoxide , adduct , stereochemistry , medicinal chemistry , organic chemistry , catalysis

Through a D IELS ‐A LDER reaction between citraconic anhydride ( 1 ) and methyl resinates, the adducts 2a, b, c were obtained. The epoxide 6 , derived from 2a , by acidic methanolysis gave 7 with retention of configuration. The structure of the latter compound was demonstrated by 7 → 8 → 9 , the dilactone 9 being characterized by an electronic interaction and an «M coupling». Sodium borohydride reduced 2d and 2a , giving the diols 3d and 3a , respectively the cis ‐configuration of which was chemically demonstrated.

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