Total Synthesis of (+)-okaramine J featuring an exceptionally facile N-reverse-prenyl to C-prenyl aza-Claisen rearrangement |
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Authors: | Roe Jennifer M Webster Richard A B Ganesan A |
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Institution: | Department of Chemistry, University of Southampton, Southampton, SO17 1BJ, United Kingdom. |
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Abstract: | reaction: see text] 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 hexahydro2,3-b]pyrroloindole to a C-prenylated derivative. |
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