4.7 Article

Toward the Synthesis of Nuphar Sesquiterpene Thioalkaloids: Stereodivergent Rhodium-Catalyzed Synthesis of the Thiolane Subunit

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 15, Pages 7581-7589

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01177

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Funding

  1. National Institutes of Health (NIGMS) [R01 GM077379]

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A stereodivergent approach to the central thiolane subunit of Nuphar sesquiterpene thioalkaloids has been developed. This approach features a rhodium-catalyzed Stevens-type rearrangement in conjunction with an enzyme resolution reaction. Further elaboration into a polycyclic ring system via alcohol oxidation and ring-closing metathesis is also described.

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