Synthetic Approach to (+/-)- Vincamine via Cleavage of an α-Diketone Monothioacetal. Alternative Synthesis of (+/-)-Eburnamine, (+/-)-Isoeburnamine, and (+/-)-Eburnamenine

DOI: 10.1039/P19800000457

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 457 - 461 (1980)

Update date:2022-08-04

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Authors:

Takano, Seiichi

Hatakeyama, Susumi

Ogasawara, Kunio

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Article abstract of DOI:10.1039/P19800000457

The half ester (8) prepared from cleavage of 2-(1,3-dithian-2-yl)-4-ethoxycarbonyl-4-ethylcyclohexanone (7) has been converted into (+/-)-eburnamine (20), (+/-)-isoeburnamine (21), and (+/-)-eburnamenine (22) by a stereospecific reaction sequence proceeding via the dithian intermediate (16).However an attempted conversion of (16) into (+/-)-vincamine (6) was unsuccessful.

Full text of DOI:10.1039/P19800000457

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