4.5 Article

A Synthesis of the Pseudopterosin A-F Aglycone

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SYNTHESIS-STUTTGART
卷 44, 期 17, 页码 2779-2785

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GEORG THIEME VERLAG KG
DOI: 10.1055/s-0032-1316643

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total synthesis; terpenoids; ring closure; rearrangement; metathesis; pericyclic reaction

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The synthesis of the pseudopterosin A-F aglycone from 3-methylcatechol features (a) the use of asymmetric Ireland-Claisen and aryl Claisen rearrangements to install three of the four stereocentres present in the molecule and (b) an A-->AB-->ABC annulation strategy using ring-closing metathesis and cationic cyclisation reactions as the key steps.

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