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Interrupted Fischer indolization approach toward the communesin alkaloids and perophoramidine.

ABSTRACT: A concise approach toward the total synthesis of the communesin alkaloids and perophoramidine is reported. The strategy relies on the use of the interrupted Fischer indolization to build the tetracyclic indoline core of the natural products. Studies to probe the scope and limitations of this plan are presented. Although the methodology does not tolerate a C8-allyl substituent en route to the challenging vicinal quaternary stereocenters, variation at C7 and on the C ring is permitted.

SUBMITTER: Schammel AW

PROVIDER: S-EPMC3445034 | biostudies-literature | 2012 Sep

REPOSITORIES: biostudies-literature

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Interrupted Fischer indolization approach toward the communesin alkaloids and perophoramidine.

Schammel Alex W AW Chiou Grace G Garg Neil K NK

Organic letters 20120820 17

A concise approach toward the total synthesis of the communesin alkaloids and perophoramidine is reported. The strategy relies on the use of the interrupted Fischer indolization to build the tetracyclic indoline core of the natural products. Studies to probe the scope and limitations of this plan are presented. Although the methodology does not tolerate a C8-allyl substituent en route to the challenging vicinal quaternary stereocenters, variation at C7 and on the C ring is permitted. ...[more]

PMID: 22905746

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