- Synthesis of (-)-sugiresinol dimethyl ether utilizing (-)-quinic acid
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(-)-Sugiresinol dimethyl ether, a derivative of (-)-sugiresinol isolated from Cryptomeria japonica, was synthesized through 1,4-conjugate addition of arylmetal reagent to a substituted chiral 2-cyclohcxcn-1-one derived from (- )quinic acid.
- Matsuo, Keizo,Sugimura, Wakiko,Shimizu, Yumiko,Nishiwaki, Keiji,Kuwajima, Hiroshi
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p. 1505 - 1513
(2007/10/05)
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- Enantioselective total synthesis of the di-O-methyl ethers of (-)-agatharesinol, (+)-hinokiresinol and (-)-sugiresinol, characteristic norlignans of Coniferae
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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.
- Muraoka, Osamu,Zheng, Bao-Zhong,Fujiwara, Noriyuki,Tanabe, Genzoh
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p. 405 - 411
(2007/10/03)
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- First asymmetric synthesis of (-)-sugiresinol dimethyl ether
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Efficient enantioselective synthesis of (-)-sugiresinol dimethyl ether was accomplished based upon two asymmetric processes: asymmetric β-alkylation of α,β-unsaturated aldimines and enantioselective dihydroxylation of olefins.
- Muraoka,Fujiwara,Tanabe,Momose
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p. 357 - 358
(2007/10/02)
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