Total synthesis of (+)-okaramine J featuring an exceptionally facile N-reverse-prenyl to C-prenyl Aza-Claisen rearrangement

Roe, Jennifer M., Webster, Richard A.B. and Ganesan, A. (2003) Total synthesis of (+)-okaramine J featuring an exceptionally facile N-reverse-prenyl to C-prenyl Aza-Claisen rearrangement. Organic Letters, 5 (16), 2825-2827. (doi:10.1021/ol034822n).

Abstract

The convergent total synthesis of (+)-okaramine J was achieved in a longest linear sequence of 12 steps from L-tryptophan tert-butyl ester. A key reaction was the acid-catalyzed room-temperature aza-Claisen rearrangement of a N-reverse-prenylated hexahydro[2,3-b]pyrroloindole to a C-prenylated derivative.

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