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Exploiting pseudo C2-symmetry for an efficient synthesis of the F-ring of the spongistatins.

ABSTRACT: A concise and efficient synthesis of the F-ring fragment of the potent antimitotic marine macrolide spongistatin 1 has been developed. The key sequence involves double cross-metathesis/Sharpless asymmetric dihydroxylation reactions to establish four stereocenters in a pseudo C2-symmetric array, followed by a selective protection reaction that breaks the pseudosymmetry, establishes a fifth stereocenter, and effectively differentiates the ester termini. Overall, the six contiguous stereocenters in the C(37)-C(45) F-ring fragment are established in just seven steps.

SUBMITTER: Tanis PS

PROVIDER: S-EPMC3845086 | biostudies-literature | 2013 Nov

REPOSITORIES: biostudies-literature

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Exploiting pseudo C2-symmetry for an efficient synthesis of the F-ring of the spongistatins.

Tanis Paul S PS Infantine Joshua R JR Leighton James L JL

Organic letters 20131010 21

A concise and efficient synthesis of the F-ring fragment of the potent antimitotic marine macrolide spongistatin 1 has been developed. The key sequence involves double cross-metathesis/Sharpless asymmetric dihydroxylation reactions to establish four stereocenters in a pseudo C2-symmetric array, followed by a selective protection reaction that breaks the pseudosymmetry, establishes a fifth stereocenter, and effectively differentiates the ester termini. Overall, the six contiguous stereocenters in ...[more]

PMID: 24111885

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Dataset Information

Exploiting pseudo C2-symmetry for an efficient synthesis of the F-ring of the spongistatins.

Publications

Exploiting pseudo C2-symmetry for an efficient synthesis of the F-ring of the spongistatins.

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