title: Alkyne Carbonyl Metathesis As a Means To Make 4-Acyl Chromenes: Syntheses of (±)-Deguelin and (±)-Munduserone.
abstract: A highly convergent synthetic approach to rotenoid natural products is described. Successful pairing of two building blocks for Sonogashira cross-coupling and intramolecular alkyne carbonyl metathesis allows ready access to 4-acylchromene, a key substructure of these natural products, leading to syntheses of (±)-deguelin and (±)-munduserone in high overall yields.
authors.affiliation: College of Pharmacy and Yonsei Institute of Pharmaceutical Sciences, Yonsei University 85 Songdogwahak-ro, Yeonsu-gu, Incheon 406-840, Republic of Korea.
authors.forename: Maloy
authors.initials: M
authors.lastname: Nayak
authors.affiliation: College of Pharmacy and Yonsei Institute of Pharmaceutical Sciences, Yonsei University 85 Songdogwahak-ro, Yeonsu-gu, Incheon 406-840, Republic of Korea.
authors.forename: Ikyon
authors.initials: I
authors.lastname: Kim
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D012402:Rotenone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D001688:Biological Products; C543754:munduserone; D012402:Rotenone; C107676:deguelin