Domino Recombinant γ‐Isomerization and Reverse Wacker Oxidation of γ‐Vinyl‐γ‐butyrolactone: Synthesis of (+)‐ trans‐ , (–)‐ and (+)‐Disparlures | Zendy

Bethi Venkati | Zendy; Kattanguru Pullaiah | Zendy; Fernandes Rodney A. | Zendy

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Domino Recombinant γ‐Isomerization and Reverse Wacker Oxidation of γ‐Vinyl‐γ‐butyrolactone: Synthesis of (+)‐ trans‐ , (–)‐ and (+)‐Disparlures

Author(s) -

Bethi Venkati,

Kattanguru Pullaiah,

Fernandes Rodney A.

Publication year - 2014

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.201400021

Subject(s) - chemistry , domino , isomerization , wacker process , stereoselectivity , cascade reaction , palladium , lactone , catalysis , stereochemistry , combinatorial chemistry , organic chemistry

A domino palladium‐catalyzed recombinant γ‐isomerization and reverse Wacker oxidation of γ‐vinyl‐γ‐butyrolactone has been explored. The strategy has been used in the stereoselective synthesis of (+)‐ trans ‐, (–)‐ and (+)‐disparlures. The synthesis was achieved in seven to eight steps from D ‐glucono‐δ‐lactone with overall yields of 19.3, 20.7 and 22.6 %, respectively.

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