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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.