Efficient Construction of Highly Substituted and Stereodefined  cis ‐Fused Lactones | Zendy

Elkhayat Zobida | Zendy; Safir Imad | Zendy; Gandara Zoila | Zendy; Retailleau Pascal | Zendy; Arseniyadis Siméon | Zendy

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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.

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