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Computationally guided organometallic chemistry: preparation of the heptacyclic pyrazine core of ritterazine N.

ABSTRACT: Diels-Alder cycloaddition of 10 followed by Wittig homologation and intramolecular diene cyclozirconation of the resulting triene under equilibrating conditions led to the tricyclic 6-6-5 ketone 5 with high diastereocontrol. The derived alpha-azido ketone 16 cyclized efficiently to the heptacyclic pyrazine core of ritterazine N.

SUBMITTER: Taber DF

PROVIDER: S-EPMC3248823 | biostudies-literature | 2006 Mar

REPOSITORIES: biostudies-literature

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Computationally guided organometallic chemistry: preparation of the heptacyclic pyrazine core of ritterazine N.

Taber Douglass F DF Taluskie Karen V KV

The Journal of organic chemistry 20060301 7

Diels-Alder cycloaddition of 10 followed by Wittig homologation and intramolecular diene cyclozirconation of the resulting triene under equilibrating conditions led to the tricyclic 6-6-5 ketone 5 with high diastereocontrol. The derived alpha-azido ketone 16 cyclized efficiently to the heptacyclic pyrazine core of ritterazine N. ...[more]

PMID: 16555834

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