Stereocontrolled total synthesis of pancratistatin.
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]
Kim
Sanghee
S
Natural Products Research Institute, Seoul National University, 28 Yungun, Jongro, Seoul 110-460, Korea.
Ko
Hyojin
H
Kim
Eunkyung
E
Kim
Deukjoon
D
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
D047151:Amaryllidaceae Alkaloids; D000903:Antibiotics, Antineoplastic; D007202:Indicators and Reagents; D007546:Isoquinolines; C044997:pancratistatin