Recently we have found that aryl hydrazide can be directly coupled to vinyl triflate to generate ene-hydrazide, the key intermediate in the Fischer indole synthesis. Heating in the presence of catalytic amount of an acid effected the [3,3]-sigmatropic rearrangement reaction <i>en route</i> to the indole product without scrambling of the indole product regiochemistry. As a further application of our regioselective indolization strategy, we have envisaged a new synthetic route to the <i>Iboga</i> family 16,21-seco indole alkaloids bearing a medium-sized C ring embedded in bridged 1-azabicyclo-[6.3.1]dodecane framework. Presented herein is our recent progress toward the asymmetric synthesis of cleavamine and quebrachamine.

Asymmetric total syntheses of bridged indole alkaloids with medium sized ring via regioselective indolization

2019 Fall National Meeting

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