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Potential intermediate, (±)-di-o-acetyl-3α-phenylselanyl-3,3a-dihydro-B-nor-6,7a- secolycorin-5-one for synthesis of the Amaryllidaceae alkaloid lycorine: Formal and total syntheses of (±)-lycorine

DOI: 10.1039/P19960000571

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 571 - 580 (1996)

Update date:2022-08-04

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Authors:

Hoshino, OsamuHoshino, Osamu

Ishizaki, MiyukiIshizaki, Miyuki

Kamei, KeisukeKamei, Keisuke

Taguchi, MinoruTaguchi, Minoru

Nagao, TakashiNagao, Takashi

Iwaoka, KiyoshiIwaoka, Kiyoshi

Sawaki, ShoheiSawaki, Shohei

Umezawa, BunsukeUmezawa, Bunsuke

Iitaka, YoichiIitaka, Yoichi

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Article abstract of DOI:10.1039/P19960000571

Formal and total syntheses of the Amaryllidaceae alkaloid, (±)-lycorine 1, were achieved by new synthetic routes via (±)-di-o-acetyl-3α-phenylselanyl-3,3a-dihydro-B-nor-6,7a- secolycorin-5-one 32. Namely, stereoselective intramolecular Diels-Alder reaction of triene ester 5 afforded, in good yield, the cis-lactone 6, which was converted into β(stereochemical)-hydroxy-γ-lactam 23. Oxidation of silyl ether 24 with m-chloroperbenzoic acid gave only β-(tert-butyldimethylsiloxy)-α-epoxide 25, the stereostructure of which was determined by its X-ray crystallographic analysis. Payne rearrangement of compound 25 and successive acetylation furnished α(stereochemical)-acetoxy-β(stereochemical)-epoxy γ-lactam 29, which was transformed into (±)-lycorine 1 by construction of the B ring. Formal total synthesis of (±)-lycorine 1 is also described.

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Product name:(E)-hexa-3,5-dienyl-3',4'-methylenedioxycinnamate

Cas No:136612-45-8

136612-45-8

R&D Labs maybe for 136612-45-8

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