Domino Recombinant γ‐Isomerization and Reverse Wacker Oxidation of γ‐Vinyl‐γ‐butyrolactone: Synthesis of (+)‐trans‐, (–)‐ and (+)‐Disparlures. Issue 15 (11th April 2014)

• Record Type: Journal Article
• Authors: Bethi, Venkati; Kattanguru, Pullaiah; Fernandes, Rodney A.
• Is Part Of: European journal of organic chemistry. Issue 15(2014)
• Page Start: 3249
• Page End: 3255
• Publication Date: 2014-04-11
• Subjects: Synthetic methods -- Asymmetric synthesis -- Cross‐metathesis -- Palladium -- Oxidation -- Pheromones; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201400021
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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 fromD ‐glucono‐δ‐lactone with overall yields of 19.3, 20.7 and 22.6 %, respectively. Abstract : A palladium‐catalyzed domino recombinant γ‐isomerization and reverse Wacker oxidation of γ‐vinyl‐γ‐butyrolactone has been explored. The building blocks synthesized therein were successfully transformed into (+)‐ trans ‐disparlure and (–)‐ and (+)‐disparlure with overall yields of 19.3, 20.7 and 22.6 %, respectively.