title: Unified total syntheses of (-)-medicarpin, (-)-sophoracarpan A, and (±)-kushecarpin A with some structural revisions.
abstract: The total syntheses of medicarpin, sophoracarpan A, and kushecarpin A from a common intermediate are achieved by using ortho- and para-quinone methide chemistry. Additionally, the relative stereochemistry of sophoracarpan A and B have been reassigned.
authors.affiliation: Department of Chemistry and Biochemistry, University of California Santa Barbara, Santa Barbara, CA, 93106-9510 (USA).
authors.forename: Zhen-Gao
authors.initials: ZG
authors.lastname: Feng
authors.forename: Wen-Ju
authors.initials: WJ
authors.lastname: Bai
authors.forename: Thomas R R
authors.initials: TR
authors.lastname: Pettus
mesh_terms: D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D036343:Pterocarpans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D000094162:Phytoalexins
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; D036343:Pterocarpans; C570379:kushecarpin A; C000601572:sophoracarpan A; C047353:medicarpin; D000094162:Phytoalexins
keywords: benzopyran acetal; diastereoselective diels-alder; oxidative dearomatization; pterocarpan; quinone methide