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Direct methoxypyridine functionalization approach to magellanine-type Lycopodium alkaloids.

ABSTRACT: A concise enantioselective approach to the tetracyclic core of the magellanine-type Lycopodium alkaloids is reported. Key to this approach is the use of the Hajos-Parrish reaction to set a challenging quaternary stereocenter, thereby guiding the stereoselectivity for the remainder of the synthesis, as well as the use of a palladium-mediated direct pyridine functionalization reaction to forge the tetracyclic core.

SUBMITTER: Murphy RA

PROVIDER: S-EPMC3262889 | biostudies-literature | 2012 Jan

REPOSITORIES: biostudies-literature

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Direct methoxypyridine functionalization approach to magellanine-type Lycopodium alkaloids.

Murphy Rebecca A RA Sarpong Richmond R

Organic letters 20111227 2

A concise enantioselective approach to the tetracyclic core of the magellanine-type Lycopodium alkaloids is reported. Key to this approach is the use of the Hajos-Parrish reaction to set a challenging quaternary stereocenter, thereby guiding the stereoselectivity for the remainder of the synthesis, as well as the use of a palladium-mediated direct pyridine functionalization reaction to forge the tetracyclic core. ...[more]

PMID: 22201223

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