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Communication | Regular issue | Vol 29, No. 6, 1989, pp.1037-1040
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5015
Structure and Absolute Configuration of the Ochrosia Alkaloid Ochromianine: Syntheses of (±)- and (—)-Ochromianine

Tozo Fujii,* Masashi Ohba, Takeshi Tachinami, Takako Ohashi, Michel Koch, and Elisabeth Seguin

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan

Abstract

The structure of the Ochrosia alkaloid ochromianine has been established as 11-methoxydihydrocorynantheol [(-)-I] as a result of the racemic and chiral syntheses of the candidate structure I. These syntheses started from the lactim ethers (±)-III and (+)-III, respectively, and proceeded through the intermediates (±)-IV, (±)-VI, and (±)-VIII and through (+)-IV, (+)-VI, and (-)-VIII, respectively.