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Oxidative carbocation formation in macrocycles: synthesis of the neopeltolide macrocycle.

ABSTRACT: Macrocyclic oxocarbenium ions can be formed from macrolactones that contain benzylic or allylic ether groups through oxidative carbon-hydrogen-bond activation mediated by 2,3-dichloro-4,5-dicyanoquinone (DDQ). The applicability of this efficient reaction to complex-molecule synthesis was demonstrated by its use in a brief formal synthesis of neopeltolide (see retrosynthetic scheme) to form the tetrahydropyrone ring.

SUBMITTER: Tu W

PROVIDER: S-EPMC2744605 | biostudies-literature | 2009

REPOSITORIES: biostudies-literature

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Oxidative carbocation formation in macrocycles: synthesis of the neopeltolide macrocycle.

Tu Wangyang W Floreancig Paul E PE

Angewandte Chemie (International ed. in English) 20090101 25

Macrocyclic oxocarbenium ions can be formed from macrolactones that contain benzylic or allylic ether groups through oxidative carbon-hydrogen-bond activation mediated by 2,3-dichloro-4,5-dicyanoquinone (DDQ). The applicability of this efficient reaction to complex-molecule synthesis was demonstrated by its use in a brief formal synthesis of neopeltolide (see retrosynthetic scheme) to form the tetrahydropyrone ring. ...[more]

PMID: 19455526

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