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Stereocontrolled Synthesis of (+)-Plagiogyrin A.

ABSTRACT: Plagiogyrin A (1) was first isolated from the fronds of Plagiogyria matsumureana. Structurally, it features an ?-ketoaldehyde functional group in its hemiacetal form, fused in a cis-substituted lactone ring. We have successfully synthesized the skeleton of this natural product by employing a stereocontrolled aldol reaction followed by the installation of the ?-ketoaldehyde moiety derived from the mild oxidation of an ?-diazoketone. Finally, anhydrous acidic conditions released the protected diol and provided the required cyclized hemiacetal.

SUBMITTER: Shi Y

PROVIDER: S-EPMC5378675 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

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Stereocontrolled Synthesis of (+)-Plagiogyrin A.

Shi Yunlong Y Pierce Joshua G JG

Organic letters 20161003 20

Plagiogyrin A (1) was first isolated from the fronds of Plagiogyria matsumureana. Structurally, it features an α-ketoaldehyde functional group in its hemiacetal form, fused in a cis-substituted lactone ring. We have successfully synthesized the skeleton of this natural product by employing a stereocontrolled aldol reaction followed by the installation of the α-ketoaldehyde moiety derived from the mild oxidation of an α-diazoketone. Finally, anhydrous acidic conditions released the protected diol ...[more]

PMID: 27690467

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