A Concise Total Synthesis of (±)-Trigonoliimine B

Trigonoliimine B, a hexacyclic alkaloid, is synthesized in seven steps from simple starting materials. The synthesis features the use of an alpha-isocyanoacetate as a glycine template for the preparation of an alpha,alpha-disubstituted alpha-amino ester that is appropriately functionalized for the construction of C, D, and E rings. Sulfolane was found to be the solvent of choice for the unprecedented Bischler-Napieralski reaction implemented for the construction of a seven-membered ring with concurrent formation of an exo-imine function.


Published in:
Organic Letters, 14, 5, 1338-1341
Year:
2012
ISSN:
1523-7052
Keywords:
Laboratories:




 Record created 2012-03-10, last modified 2018-03-17


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