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Approach toward the total synthesis of 5-hydroxyaloin A.

ABSTRACT: The synthesis of a thiomethyl analogue of 5-hydroxyaloin A has been achieved using benzyne and naphthyne [4 + 2] cycloadditions with substituted furans. A regiocontrolled cycloaddition was achieved using a silicon tether, and a regioselective ring opening was accomplished using a sulfide as a directing group.

SUBMITTER: Procko KJ

PROVIDER: S-EPMC3005804 | biostudies-literature | 2010 Dec

REPOSITORIES: biostudies-literature

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Approach toward the total synthesis of 5-hydroxyaloin A.

Procko Kristen J KJ Li Hui H Martin Stephen F SF

Organic letters 20101117 24

The synthesis of a thiomethyl analogue of 5-hydroxyaloin A has been achieved using benzyne and naphthyne [4 + 2] cycloadditions with substituted furans. A regiocontrolled cycloaddition was achieved using a silicon tether, and a regioselective ring opening was accomplished using a sulfide as a directing group. ...[more]

PMID: 21082813

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