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Asymmetric alcohol C-H allylation and syn-crotylation: C9-C20 of tetrafibricin.

ABSTRACT: The C9-C20 segment of the fibrinogen receptor inhibitor tetrafibricin was prepared in 10 steps (longest linear sequence). Ruthenium catalyzed enantioselective syn-crotylation is used to construct C9-C13. Iridium catalyzed asymmetric alcohol C-H allylation of a commercial malic acid derived alcohol is used to construct C14-C20. Recovery and recycling of the iridium catalyst is described.

SUBMITTER: Itoh T

PROVIDER: S-EPMC3932543 | biostudies-literature | 2014 Feb

REPOSITORIES: biostudies-literature

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Asymmetric alcohol C-H allylation and syn-crotylation: C9-C20 of tetrafibricin.

Itoh Takahiko T Montgomery T Patrick TP Recio Antonio A Krische Michael J MJ

Organic letters 20140114 3

The C9-C20 segment of the fibrinogen receptor inhibitor tetrafibricin was prepared in 10 steps (longest linear sequence). Ruthenium catalyzed enantioselective syn-crotylation is used to construct C9-C13. Iridium catalyzed asymmetric alcohol C-H allylation of a commercial malic acid derived alcohol is used to construct C14-C20. Recovery and recycling of the iridium catalyst is described. ...[more]

PMID: 24422777

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