22338-53-0Relevant academic research and scientific papers
Synthesis of norlignans and in vitro inhibitory activity of antigen-induced degranulation
Park, Eonjeong,Yang, Yoon Jung,Kim, Aejin,Kwak, Jong Hwan,Jung, Young Hoon,Kang, Se Chan,Kim, In Su
supporting information; experimental part, p. 3653 - 3655 (2012/07/16)
The synthesis and biological evaluation of a series of novel norlignans are described. Norlignans were evaluated for their inhibitory activity on the release of β-hexosaminidase, a marker of degranulation, from RBL-2H3 cells induced by the IgE-antigen com
Enantioselective total synthesis of the di-O-methyl ethers of (-)-agatharesinol, (+)-hinokiresinol and (-)-sugiresinol, characteristic norlignans of Coniferae
Muraoka, Osamu,Zheng, Bao-Zhong,Fujiwara, Noriyuki,Tanabe, Genzoh
, p. 405 - 411 (2007/10/03)
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.
