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49. Synthesis of (+)-Greek Tobacco Lactone via a Diastereoablative Epoxidation and a Selenium-Catalyzed Oxidative Cyclization

S. Leisering, I. Riaño, C. Depken, L. J. Gross, M. Weber, D. Lentz, R. Zimmer, C. B. W. Stark, A. Breder, M. Christmann

An asymmetric synthesis of the C11-homoterpenoid (+)-Greek tobacco lactone is developed starting from readily available (R)-linalool. The synthesis is comprised of four operations and features a diastereoablative epoxidation and an oxidative tetrahydropyran formation using vanadium-, palladium-, and selenium-catalyzed cyclizations.

Title
49. Synthesis of (+)-Greek Tobacco Lactone via a Diastereoablative Epoxidation and a Selenium-Catalyzed Oxidative Cyclization
Author
S. Leisering, I. Riaño, C. Depken, L. J. Gross, M. Weber, D. Lentz, R. Zimmer, C. B. W. Stark, A. Breder, M. Christmann
Identifier
DOI: 10.1021/acs.orglett.7b00484
Citation
Org. Lett. 2017, 19, 1478–1481.