Phytochemistry

An unusual epimerization of the α-OH-1 group of the norditerpenoid alkaloid delphisine

SW Pelletier, HK Desai, Q Jiang, SA Ross

Index: Pelletier, S. William; Desai, Haridutt K.; Jiang, Quingping; Ross, Samir A. Phytochemistry (Elsevier), 1990 , vol. 29, # 11 p. 3649 - 3652

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Citation Number: 11

Abstract

Abstract Solvolysis of delphisine in refluxing methanol gives 8-deacetyl-8-O-methyl-1-epi- delphisine. Similarly, hydrolysis of delphisine in boiling water affords 14-O-acetyl-1-epi- neoline and solvolysis of 8-O-acetylneoline in methanol gives 8-O-methyl-1-epi-neoline. The structures of the products have been proved by spectral data and comparison with authentic samples. For epimerization to occur, both a α-OH-1 and a OAc-8 group are necessary. ...