Welcome to LookChem.com Sign In|Join Free

Article Doi

Enantioselective total synthesis of the di-O-methyl ethers of (-)-agatharesinol, (+)-hinokiresinol and (-)-sugiresinol, characteristic norlignans of Coniferae

DOI: 10.1039/P19960000405

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 405 - 411 (1996)

Update date:2022-09-26

Topics:

Authors:

Muraoka, OsamuMuraoka, Osamu

Zheng, Bao-ZhongZheng, Bao-Zhong

Fujiwara, NoriyukiFujiwara, Noriyuki

Tanabe, GenzohTanabe, Genzoh

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/P19960000405

Facile enantioselective syntheses of the di-O-methyl ethers of the norlignans, (-)-agatharesinol (-)-1a, (+)-hinokiresinol (+)-2a and (-)-sugiresinol (-)-3a are described. Grignard addition of vinylmagnesium bromide to an aldimine (-)-13, prepared from the tert-butyl ester 11 and 4-methoxycinnamaldehyde 12, afforded a homochiral vinyl aldehyde, (-)-3-(4-methoxyphenyl)pent-4-enal (-)-14 in > 95% ee, which was converted into a diastereoisomeric mixture of 1,3-bis(4-methoxyphenyl)pent-4-en-1-ols (3R)-6 by a second Grignard reaction with 4-methoxyphenylmagnesium bromide. Sharpless' asymmetric dihydroxylation of the vinyl alcohols (3R)-6 proceeded diastereoselectively to give the triol of desired relative stereochemistry (2S,3S)-7. This, upon dehydration, afforded (-)-di-O-methylsugiresinol (-)-3b, the subsequent acid-catalysed cyclization of which gave (-)-di-O-methyl agatharesinol (-)-1b. (+)-Di-O-methylhinokiresinol (+)-2b was readily obtained by the dehydration of the vinyl alcohols (3R)-6.

View More

Products guided by the article

Product name:1,3-Bis(4-methoxyphenyl)pent-4-en-1-ol

Cas No:135966-00-6

135966-00-6

R&D Labs maybe for 135966-00-6

Relevant to this article

Hot Product