Fusao Kido
Tohoku University
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Featured researches published by Fusao Kido.
Tetrahedron | 1990
Fusao Kido; Subhash C. Sinha; Toshiya Abiko; Masataka Watanabe; Akira Yoshikoshi
Abstract The rhodium (II) acetate-catalyzed [2,3]sigma-tropic rearrangement of the diazo malonates of ( z )-4-phen-ylthio-2-buten-l-ol derivatives 6 afforded vinyl-substituted butyrolactones 10 in a highly stereoselective manner, while the rearrangement of the diazo malonates of homologues, ( z )-5-phenylthio-3-penten-1-ol derivatives 9, yielded vinyl-substituted valerolactones 13 and 14 in the predominance of the formers. A stereochemically fixed substituent R in 9 was found to be an important factor resulting to high stereoselectivity in the latter rearrangement as shown by using diazo malonate 20b as substrate.
Tetrahedron Letters | 1989
Fusao Kido; Subhash C. Sinha; Toshiya Abiko; Akira Yoshikoshi
α-Diazomalonates of (Z)-4-phenylthio-2-buten-1-ol homologues (2) stereoselectively provided γ-alkyl-α-ethoxycarbonyl-α-phenylthio-β-vinylbutyrolactones (1) by the [2.3]sigmatropic rearrangement of cyclic sulfonium ylides (3) intramolecularly generated therefrom with rhodium acetate.
Tetrahedron | 1995
Fusao Kido; Kazuo Yamaji; Subhash C. Sinha; Toshiya Abiko; Michiharu Kato
Abstract The rhodium(II)-catalyzed cyclization of acyclic α-diazo-β-keto esters 1c,d provided stereoselectively the highly substituted cyclohexanones 3c,d respectively, by the [2,3]sigmatropic rearrangement via stereocontrolled nine-membered allylsulfonium ylides 2c,d. Further elaboration of 3d toward the cyclohexanone 36 accomplished asymmetric formal syntheses of the representative elemanoids, 37 and 38. The compound 3c was transformed into the cyclohexanone 34a and cyclohexene 43, which could serve as the key intermediates for the synthesis of natural products possessing contigously cis-arranged trimethylcyclohexanone and its related moieties, respectively.
Tetrahedron | 1987
Fusao Kido; Yoshihiro Noda; Akira Yoshikoshi
Abstract A new synthetic approach to dl -paniculide A (1) based on the annulation of 2-formylpropionate with α-phenylthio-β-vinylbutenolide 4 is described. The annulation products 6a–6c was dehydrated to give 7 , and the sulfoxide of 7 was submitted to sulfoxide-sulfinate rearrangement in aqueous media to yield 8a and 8b . The latter was converted to the former by configurational inversion of its hydroxyl group. Saturated lactone 11a obtained from 8a was homoprenylated, and after desilylation, the product 12b was selenenylated to give 13a . Alkaline hydrolysis followed by oxidative elimination of the selenenyl group provided 14a , which was then acetylated and oxidized with lead tetraacetate to yield 15a and 16a–16c . dl -Paniculide A was derived from 15a and 16a via 18a .
Tetrahedron | 1973
N. Hanayama; Fusao Kido; R. Tanaka; Hisashi Uda; Akira Yoshikoshi
Abstract Two sesquiterpene car☐ylic acids, zizanoic and epizizanoic acids, were isolated from the essential oil of vetiver and were assigned the structures1a and2a on the basis of chemical degradation. Although khusimol and zizaene (tricyclovetivene) had been assigned structures previously, the current work revealed that these sesquiterpenoids also belong to the zizaane group and that the formulae should be revised as1b and1c, respectively.
Tetrahedron Letters | 1991
Fusao Kido; Yasuhiko Kawada; Michiharu Kato; Akira Yoshikoshi
endo-4-Ethoxycarbonyl-4-(phenylthio)-9-methylene-2-oxabicyclo-[3.3.1]nonan-3-ones (5a–c) and their related compounds 5e–h, endo-4-ethoxycarbonyl-4-(phenylthio)-8-methylene-2-oxabicyclo[3.2.1]octan-3-one (5d) were synthesized from α-diazomalonates 3 of 2-(phenylthio)cyclohex-2-en-1-ols (1a–c) and their related compounds e–h, and 2-(phenylthio)cyclopent-2-en-1-ol (1d), respectively, via the [2,3]sigmatropic rearrangement of cyclic allylsulfonium ylides 4.
Heterocycles | 1991
Fusao Kido; Toshiya Abiko; Abul B. Kazi; Michiharu Kato; Akira Yoshikoshi
Treatment of the α-diazomalonates (5a-c) of 2-[(2-phenylthiomethyl)-1-cycloalkenyl]ethanols with rhodium acetate led to the [2,3] sigmatropic rearrangement of the cyclic allylsulfonium ylides (6a-c) to give the spiro-fused δ-valerolactones (7a-c) in excellent yields. Similarly, the spiro-fused γ-butyrolactone (10) was prepared starting with the α-diazomalonate of [(2-phenylthiomethyl)-1-cyclohexenyl]methanol analog
Journal of The Chemical Society-perkin Transactions 1 | 1992
Fusao Kido; Toshiya Abiko; Michiharu Kato
A spiroannulation reaction using the [2,3]sigmatropic rearrangement via a cyclic allylsulfonium ylide was developed and applied to the synthesis of (+)-acorenone B starting from (–)-perillaldehyde.
Journal of The Chemical Society, Chemical Communications | 1975
Fusao Kido; Toshio Fujishita; Kentaro Tsutsumi; Akira Yoshikoshi
With β-vinylbutenolide 2-methylcyclohexane-1,3-dione or 2-ethoxycarbonylcyclohexanone undergoes 1,6-Michael addition and subsequent cyclisation yielding the annelation product.
Heterocycles | 1992
Michiharu Kato; Fusao Kido; Abul B. Kazi; Kazuo Yamaji; Akira Yoshikoshi
Treatment of the diazomalonates (9a-d) of 2-phenylthio-3-butenol derivatives with catalytic rhodium acetate resulted in the [2,3]sigmatropic rearrangement of six-membered allylsulfonium ylides to provide γ,δ-unsaturated seven-membered lactones (10a-d) in good yields