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Diels-Alder routes to angularly halogenated cis-fused bicyclic ketones: Readily accessible cyclynone intermediates.

ABSTRACT: We have developed an efficient Lewis acid-catalyzed Diels-Alder route to a series of cis-fused bicyclic ketones bearing quaternary halogenation at the angular position. We have also developed a Diels-Alder based one-flask method for the regioselective preparation of TBS-protected 6-hydroxy tetralone and 5-hydroxy indanone derivatives.

SUBMITTER: Lee JH

PROVIDER: S-EPMC2936481 | biostudies-literature | 2010 Sep

REPOSITORIES: biostudies-literature

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Diels-Alder routes to angularly halogenated cis-fused bicyclic ketones: Readily accessible cyclynone intermediates.

Lee Jun Hee JH Danishefsky Samuel J SJ

Tetrahedron letters 20100901 35

We have developed an efficient Lewis acid-catalyzed Diels-Alder route to a series of cis-fused bicyclic ketones bearing quaternary halogenation at the angular position. We have also developed a Diels-Alder based one-flask method for the regioselective preparation of TBS-protected 6-hydroxy tetralone and 5-hydroxy indanone derivatives. ...[more]

PMID: 20835369

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