A short and expeditious synthesis of Luotonin A, and its analogues along with Vasicinone and its analogues has been achieved via a tricyclic key intermediate that was inturn accessed from simple substrates employing Dieckman condensation as a key step. Additionally, in the process we have uncovered some interesting transformations - tandem decarboxylative reduction of  beta-ketoester to access, and Barbier mediated Friendlander condensations to access a small library of substituted Luotonins. Synthesis and biological evlauation details of the library will be presented.

Efficient approach to pyrroloquinazolinone alkaloids: Vasicinone and luotonin A

2019 Fall National Meeting

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