4825-70-1Relevant academic research and scientific papers
Practical Synthesis of (±)-Nyasol
Fang, Yuanying,Park, Haeil
, p. 137 - 142 (2015/10/20)
A practical total synthesis of racemic nyasol (7) was explored. The α-hydroxyketo compound 3 was prepared from commercially available starting materials in two steps. Chelation-controlled reduction of the α-hydroxyketo compound 3 with Zn(BH4)s
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.
MEDICINAL PLANTS OF SOUTHERN AFRICA. PART 2. SYNTHESIS OF 1,3-BIS-(4-METHOXYPHENYL)PENTA-1,4-DIENE, A STEREOISOMER OF DIMETHYLHINOKIRESINOL, AND ITS 4-MONOMETHOXY ANALOGUE
Ameer, Farouk,Drewes, Siegfried E.,Drewes, Mark W.,Roos, Gregory H. P.,Watson, Martin C.
, p. 1425 - 1430 (2007/10/02)
A six-step synthesis of the title compounds (6) and (7) from prop-2-yn-1-ol, and proceeding via 3-(4-methoxyphenyl)prop-1-yne, is described.Detailed 1H n.m.r. spectral analysis (500 MHz) suggests that the synthetic compounds have a 1,2-E stereochemistry in contrast to the Z-configuration present in the naturally occurring hinokiresinol (3).By utilizing a different, and much less efficient route, a small quantity of (Z)-3-(4-methoxyphenyl)-1-phenylpenta-1,4-diene (5) was obtained.
