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A palladium-catalyzed carbo-oxygenation: the bielschowskysin case.

ABSTRACT: An asymmetric synthesis of an advanced tetracyclic intermediate toward the synthesis of bielschowskysin (1) is described. A biomimetic [2 + 2]-photocyclization was used to establish the cyclobutane core of bielschowskysin. Macrocyclization under Heck conditions led to an unprecedented carbo-oxygenation of a 1,1-disubstituted double bond.

SUBMITTER: Himmelbauer M

PROVIDER: S-EPMC3691719 | biostudies-literature | 2013 Jun

REPOSITORIES: biostudies-literature

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A palladium-catalyzed carbo-oxygenation: the bielschowskysin case.

Himmelbauer Martin M Farcet Jean-Baptiste JB Gagnepain Julien J Mulzer Johann J

Organic letters 20130531 12

An asymmetric synthesis of an advanced tetracyclic intermediate toward the synthesis of bielschowskysin (1) is described. A biomimetic [2 + 2]-photocyclization was used to establish the cyclobutane core of bielschowskysin. Macrocyclization under Heck conditions led to an unprecedented carbo-oxygenation of a 1,1-disubstituted double bond. ...[more]

PMID: 23724910

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