- Total synthesis of epoxyquinols A, B, and C and epoxytwinol A and the reactivity of a 2H-pyran derivative as the diene component in the Diels-Alder reaction
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(Chemical Equation Presented). Full details of two versions of the total synthesis of epoxyquinols A, B, and C and epoxytwinol A (RKB-3564D) are described. In the first-generation synthesis, the HfCL4-mediated diastereoselective Diels-Alder rea
- Shoji, Mitsuru,Imai, Hiroki,Mukaida, Makoto,Sakai, Ken,Kakeya, Hideaki,Osada, Hiroyuki,Hayashi, Yujiro
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- Novel non-peptide inhibitors targeting death receptor-mediated apoptosis
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We have previously reported that ECH, (2R, 3R, 4S)-2,3-epoxy-4-hydroxy-5-hydroxymethyl-6-(1E)-propenyl-cyclohex-5-en-1-one inhibits Fas-mediated apoptosis by blocking self-activation of pro-caspase-8 in the death-inducing signaling complex (DISC). A series of ECH derivatives were asymmetrically synthesized via key synthetic intermediates obtained from lipase-catalyzed kinetic resolution. Inhibitory activities of the derivatives towards death receptor-mediated apoptosis both in type I and type II cells were investigated, revealing that novel non-peptide inhibitors, RKTS-33 and RKTS-34, are effective as ECH.
- Kakeya, Hideaki,Miyake, Yasunobu,Shoji, Mitsuru,Kishida, Satoshi,Hayashi, Yujiro,Kataoka, Takao,Osada, Hiroyuki
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p. 3743 - 3746
(2007/10/03)
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- A practical total synthesis of both enantiomers of epoxyquinols A and B
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A practical total synthesis of both enantiomers of epoxyquinols A and B has been developed. Key reactions are the chromatography-free preparation of an iodolactone by using acryloyl chloride as dienophile in the Diels-Alder reaction of furan, the lipase-mediated kinetic resolution of a cyclohexenol derivative, and a modified procedure for α-iodonation of a cyclohexenone.
- Shoji, Mitsuru,Kishida, Satoshi,Takeda, Mitsuhiro,Kakeya, Hideaki,Osada, Hiroyuki,Hayashi, Yujiro
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p. 9155 - 9158
(2007/10/03)
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- Total synthesis of (+)-epoxyquinols A and B
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A highly stereoselective HfCl4-mediated Diels-Alder reaction of furan and the chiral acrylate ester of Corey's auxiliary to subsequently give 1, and the realization of the postulated biosynthetic pathway for the construction of epoxyquinols A a
- Shoji, Mitsuru,Yamaguchi, Junichiro,Kakeya, Hideaki,Osada, Hiroyuki,Hayashi, Yujiro
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p. 3192 - 3194
(2007/10/03)
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- Synthesis of (3R)- and (3S)-fluoro-(4R,5R)-dihydroxy-1-cyclohexene-1- carboxylic acids: The (3R)- and (3S)-fluoro analogues of (-)-shikimic acid
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(3R)-and (3S)-Fluoro-(4R,5R)-dihydroxy-1-cyclohexene-1-carboxylic acids (the (3R)- and (3S)-fluoro analogues of (-)-shikimic acid) have been synthesised from (-)-shikimic acid via an intermediate epoxide (a fungal metabolite from Chalara microspora) that
- Brettle,Cross,Frederickson,Haslam,MacBeath,Davies
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p. 1275 - 1278
(2007/10/03)
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- The shikimate pathway. Part 9. Halogenation at C-3 of the shikimate nucleus
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The use of (-)-shikimic acid as starting material in the syntheses of a series of C-3 halogenated derivatives including the analogous 3α- and 3β-fluoro and 3β-chloro acids is described together with the first stereospecific synthesis of (-)-3-epi-shikimic acid directly from the parent acid.
- Brettle, Roger,Cross, Richard,Frederickson, Martyn,Haslam, Edwin,MacBeath, Fiona S.,Davies, Gareth M.
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p. 10547 - 10556
(2007/10/03)
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- Synthesis of (-)-3(R)-amino-4(R),5(R)-dihydroxy-1-cyclohexene-1-carboxylic acid: The 3(R)-amino analogue of (-)-shikimic acid
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(-)-3(R)-Amino-4(R),5(R)-dihydroxy-1-cyclohexene-1-carboxylic acid (the 3(R)-amino analogue of (-)-shikimic acid) has been synthesised from (-)-shikimic acid in seven steps. Copyright
- Brettle, Roger,Cross, Richard,Frederickson, Martyn,Haslam, Edwin,Davies, Gareth M.
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p. 291 - 294
(2007/10/03)
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- ON THE STRUCTURE OF NATURALLY-OCCURRING (+)-METHYL 3,4-ANHYDROSHIKIMATE
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A two-step synthesis of enantiomerically pure (+)-methyl 3,4-anhydroshikimate 2 from (-)- methyl shikimate 3 is described, leading to a revision in the properties reported for this natural product.
- Wood, Harold B.,Ganem, Bruce
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p. 6257 - 6258
(2007/10/02)
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- SHIKIMIC ACIDS FROM FURAN; METHODS OF STEREOCONTROLLED ACCESS TO 3,4,5-TRIOXIGENATED CYCLOHEXENES
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Oxabicycloheptenes 1 and 2 are converted to 3,4,5-oxigenated cyclohexenes by stereocontrolled hydroxylations and epoxidations coupled with reverse-Michael cleavage of the oxabicyclo system.Three epimers of shikimic acid are synthesized by these methods.
- Rajapaksa, D.,Keay, B. A.,Rodrigo, R.
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p. 826 - 828
(2007/10/02)
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- Structure and Synthesis of the Methyl Ester of 3,4-Anhydroshikimic Acid, Isolated from a Chalara Sp.
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The methyl ester of (+)-3,4-anhydroshikimic acid has been isolated from the fungus Chalara microspora (Corda) Hughes.The structure was elucidated by spectroscopy, and was confirmed by synthesis of the title compound and its 5-epimer.Synthesis via a partia
- Fex, Tomas,Trofast, Jan,Wickberg, Boerje
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