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Studies toward the synthesis of spirolides: assembly of the elaborated E-ring fragment.

ABSTRACT: A stereoselective synthesis of the spiroimine fragment of spirolide C is described. The congested C7 and C29 tertiary and quaternary centers are constructed by a diastereoselective Ireland-Claisen rearrangement. The E ring is completed by means of an aldol cyclocondensation. Additional studies were preformed on the advanced intermediate to probe a future coupling strategy.

SUBMITTER: Stivala CE 

PROVIDER: S-EPMC2756537 | biostudies-literature | 2009 Feb

REPOSITORIES: biostudies-literature

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Studies toward the synthesis of spirolides: assembly of the elaborated E-ring fragment.

Stivala Craig E CE   Zakarian Armen A  

Organic letters 20090201 4

A stereoselective synthesis of the spiroimine fragment of spirolide C is described. The congested C7 and C29 tertiary and quaternary centers are constructed by a diastereoselective Ireland-Claisen rearrangement. The E ring is completed by means of an aldol cyclocondensation. Additional studies were preformed on the advanced intermediate to probe a future coupling strategy. ...[more]

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