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Synthesis of cananodine by intramolecular epoxide opening.

ABSTRACT: Cananodine is a guaipyridine alkaloid with activity against liver cancer. Cananodine was synthesized using a remarkable intramolecular opening of a trisubstituted epoxide as the key step in construction of the seven-membered carbocycle of the target. The epoxide opening strategy allows all four stereoisomers of cananodine to be prepared.

SUBMITTER: Shelton P 

PROVIDER: S-EPMC5722248 | biostudies-other | 2017 Aug

REPOSITORIES: biostudies-other

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Synthesis of cananodine by intramolecular epoxide opening.

Shelton Patrick P   Ligon Toby J TJ   Dell Née Meyer Jennifer M JM   Yarbrough Loagan L   Vyvyan James R JR  

Tetrahedron letters 20170725 35

Cananodine is a guaipyridine alkaloid with activity against liver cancer. Cananodine was synthesized using a remarkable intramolecular opening of a trisubstituted epoxide as the key step in construction of the seven-membered carbocycle of the target. The epoxide opening strategy allows all four stereoisomers of cananodine to be prepared. ...[more]