title: Stereocontrolled total synthesis of pancratistatin.
abstract: A new total synthesis of the antitumor alkaloids, pancratistatin (1), has been accomplished from readily available staring materials. The Claisen rearrangement of dihydropyranethylene 5 was employed to construct the A and C rings. Stereo- and regiocontrolled functional group interchange, such as iodolactonization, dihydroxylations, and a cyclic sulfate elimination reaction, allows for the production of the target natural product. [reaction: see text]
authors.affiliation: Natural Products Research Institute, Seoul National University, 28 Yungun, Jongro, Seoul 110-460, Korea.
authors.forename: Sanghee
authors.initials: S
authors.lastname: Kim
authors.forename: Hyojin
authors.initials: H
authors.lastname: Ko
authors.forename: Eunkyung
authors.initials: E
authors.lastname: Kim
authors.forename: Deukjoon
authors.initials: D
authors.lastname: Kim
mesh_terms: D047151:Amaryllidaceae Alkaloids; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D010946:Plants, Medicinal / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D047151:Amaryllidaceae Alkaloids; D000903:Antibiotics, Antineoplastic; D007202:Indicators and Reagents; D007546:Isoquinolines; C044997:pancratistatin