A synthesis of the carbon skeleton of maoecrystal V.
An enantioselective synthesis of the maoecrystal V (1) carbon skeleton is described. The key transformations include arylation of a 1,3-dicarbonyl compound with a triarylbismuth(V) dichloride species, oxidative dearomatization of a phenol, and a subsequent intramolecular Diels-Alder reaction.
Krawczuk
Paul J
PJ
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Schöne
Niklas
N
Baran
Phil S
PS
D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004365:Drugs, Chinese Herbal / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D037602:Isodon / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
D004224:Diterpenes; D004365:Drugs, Chinese Herbal; C473434:maoecrystal A