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Transmissive olefination route to putative "morinol I" lignans.

ABSTRACT: A series of morinol-type lignans were rapidly assembled using a Grignard-based transmissive olefination. In combination with palladium-catalyzed arylations, the strategy provides stereoselective access to (7Z,7'E), (7E,7'E), and (7E,7'Z) morinol diastereomers and the (7Z,8'E) and (7E,8'E) conjugated analogues. Critical for the E/Z stereoselectivity is a new, general method for converting alkenenitriles to alkenemethanols that circumvents the enal E/Z isomerization commonly encountered during conventional i-Bu(2)AlH reduction.

SUBMITTER: Yao L

PROVIDER: S-EPMC3331789 | biostudies-literature | 2012 Apr

REPOSITORIES: biostudies-literature

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Transmissive olefination route to putative "morinol I" lignans.

Yao Lihua L Pitta Bhaskar B Ravikumar P C PC Purzycki Matthew M Fleming Fraser F FF

The Journal of organic chemistry 20120320 7

A series of morinol-type lignans were rapidly assembled using a Grignard-based transmissive olefination. In combination with palladium-catalyzed arylations, the strategy provides stereoselective access to (7Z,7'E), (7E,7'E), and (7E,7'Z) morinol diastereomers and the (7Z,8'E) and (7E,8'E) conjugated analogues. Critical for the E/Z stereoselectivity is a new, general method for converting alkenenitriles to alkenemethanols that circumvents the enal E/Z isomerization commonly encountered during con ...[more]

PMID: 22432777

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