Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 22, Pages 8384-8389Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo061270o
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A convergent synthesis of the naturally occurring alkaloid Calothrixin B is presented, which used a regioselective hetero-Diels-Alder reaction between a push-pull 2-aza-diene and a N-protected 3-bromo-9H- carbazole-1,4-dione to construct the five-ring skeleton of the molecule. Protection of the indole motif with a benzyl group was unattractive for delivery of sufficient target material because the removal of the protecting group had not been high yielding. We therefore elected to temporarily protect the indole motif with a more labile benzyloxycarbonyl group. Accordingly, the synthesis of calothrixin B proceeded in 17% overall yield over 9 steps from the commercially available 1,2,3,9-tetrahydro-4H-carbazol-4-one.
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