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Efficient Construction of Highly Substituted and Stereodefined cis ‐Fused Lactones
Author(s) -
Elkhayat Zobida,
Safir Imad,
Gandara Zoila,
Retailleau Pascal,
Arseniyadis Siméon
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000556
Subject(s) - chemistry , oxidizing agent , reagent , ring (chemistry) , electrophile , sequence (biology) , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , biochemistry
The methodology described in this paper involves the epoxidation of cyclic ene‐acetals to spontaneously generate 6α‐hydroxy‐bis‐acetals that could serve as precursors for a Cannizzaro‐type rearrangement, yielding bis‐angularly substituted cis ‐fused lactones. Both the oxidizing reagent, m ‐CPBA or NaBO 3 , and the substitution pattern can be important in determining the course of the epoxidation/ring‐opening sequence, with NaBO 3 being the ideal electrophilic oxidant for the epoxidation/spontaneous ring‐opening/ring‐system interchange sequence.