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Total synthesis of neopeltolide and analogs.

ABSTRACT: Neopeltolide, a potent cytotoxin from a Carribean sponge, was synthesized through a brief sequence that highlights the use of ethers as oxocarbenium ion precursors. Other key steps include an acid-mediated etherification and sequence that features a Sonogashira reaction, an intramolecular alkyne hydrosilylation reaction, and a Tamao oxidation. The alkene that is required for the oxidative cyclization can be hydrogenated to provide access to the natural product or an epimer, or can be epoxidized or dihydroxylated to form polar analogs.

SUBMITTER: Cui Y

PROVIDER: S-EPMC2917233 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature

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Total synthesis of neopeltolide and analogs.

Cui Yubo Y Tu Wangyang W Floreancig Paul E PE

Tetrahedron 20100601 26

Neopeltolide, a potent cytotoxin from a Carribean sponge, was synthesized through a brief sequence that highlights the use of ethers as oxocarbenium ion precursors. Other key steps include an acid-mediated etherification and sequence that features a Sonogashira reaction, an intramolecular alkyne hydrosilylation reaction, and a Tamao oxidation. The alkene that is required for the oxidative cyclization can be hydrogenated to provide access to the natural product or an epimer, or can be epoxidized ...[more]

PMID: 20697460

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