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Multicomponent assembly processes for the synthesis of diverse yohimbine and corynanthe alkaloid analogues.

ABSTRACT: A strategy involving a Mannich-type multicomponent assembly process followed by a 1,3-dipolar cycloaddition has been developed for the rapid and efficient construction of parent heterocyclic scaffolds bearing indole and isoxazolidine rings. These key intermediates were then readily elaborated using well-established protocols for refunctionalization and cross-coupling to access a diverse 180-member library of novel pentacyclic and tetracyclic compounds related to the Yohimbine and Corynanthe alkaloids. Several other new multicomponent assembly processes were developed to access dihydro-?-carboline-fused benzodiazepines, pyrimidinediones, and rutaecarpine derivatives.

SUBMITTER: Granger BA

PROVIDER: S-EPMC3800219 | biostudies-other | 2013 Jul

REPOSITORIES: biostudies-other

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Multicomponent assembly processes for the synthesis of diverse yohimbine and corynanthe alkaloid analogues.

Granger Brett A BA Wang Zhiqian Z Kaneda Kyosuke K Fang Zhenglai Z Martin Stephen F SF

ACS combinatorial science 20130604 7

A strategy involving a Mannich-type multicomponent assembly process followed by a 1,3-dipolar cycloaddition has been developed for the rapid and efficient construction of parent heterocyclic scaffolds bearing indole and isoxazolidine rings. These key intermediates were then readily elaborated using well-established protocols for refunctionalization and cross-coupling to access a diverse 180-member library of novel pentacyclic and tetracyclic compounds related to the Yohimbine and Corynanthe alka ...[more]

PMID: 23697376

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