title: Toward the Synthesis of Nuphar Sesquiterpene Thioalkaloids: Stereodivergent Rhodium-Catalyzed Synthesis of the Thiolane Subunit.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States.
authors.forename: Ping
authors.initials: P
authors.lastname: Lu
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States.
authors.forename: Aaron T
authors.initials: AT
authors.lastname: Herrmann
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States.
authors.forename: Armen
authors.initials: A
authors.lastname: Zakarian
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D031654:Nuphar / Q000737:chemistry*; D010084:Oxidation-Reduction; D012238:Rhodium / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000470:Alkaloids; D012717:Sesquiterpenes; D013438:Sulfhydryl Compounds; D012238:Rhodium