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An unexpected effect of acetal stereochemistry on the course of its reductive cleavage.


ABSTRACT: Alternate routes to the BC spirocycle of 'upenamide starting from Diels-Alder adduct 1 are described. Key to utilizing 1 in a synthesis of 'upenamide is the differentiation of three functionalized carbons by either oxidation or protection state. A surprising effect of acetal stereochemistry on reaction course was observed and rationalized.

SUBMITTER: Wenzler ME 

PROVIDER: S-EPMC7451082 | biostudies-literature | 2016 Jul

REPOSITORIES: biostudies-literature

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An unexpected effect of acetal stereochemistry on the course of its reductive cleavage.

Wenzler Marta E ME   Sulikowski Gary A GA  

Tetrahedron letters 20160616 30


Alternate routes to the BC spirocycle of 'upenamide starting from Diels-Alder adduct <b>1</b> are described. Key to utilizing <b>1</b> in a synthesis of 'upenamide is the differentiation of three functionalized carbons by either oxidation or protection state. A surprising effect of acetal stereochemistry on reaction course was observed and rationalized. ...[more]

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