Tetrahedron Letters p. 5413 - 5416 (1994)
Update date:2022-08-03
Topics:
Sreenivasa Reddy
Cook, James M.
The total synthesis of roeharmine 1 as well as an enantiospecific synthesis of (-)-1,2,3,4-tetrahydroroeharmine 2 has been achieved via 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.
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Doi:10.1021/ja00091a010
(1994)Doi:10.1016/0022-4596(88)90253-8
(1988)Doi:10.1002/adfm.201302294
(2014)Doi:10.1021/acs.jmedchem.5b00932
(2015)Doi:10.1007/s12039-013-0506-7
(2013)Doi:10.1021/jo01267a109
(1968)
