The synthesis of roeharmine and (−)-1, 2, 3, 4-tetrahydroroeharmine

MS Reddy, JM Cook

Index: Sreenivasa Reddy; Cook, James M. Tetrahedron Letters, 1994 , vol. 35, # 30 p. 5413 - 5416

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Citation Number: 31

Abstract

The total synthesis of roeharmine 1 as well as an enantiospecific synthesis of (−)-1,2,3,4-tetrahydroroeharmine 2 has been achieved the Pictet-Spengler reaction as a key step. The optical rotation of synthetic (−)-2 was found to be higher than that reported for the natural product. A possible mechanism for the racemization of 2 upon exposure to acid has been proposed and serves as a warning to alkaloid chemists who isolate ring-A alkoxylated indole alkaloids under acidic conditions.