- Synthesis of (+)-muscarine from (S)-(-)-5-hydroxymethyl-2(5H)-furanone
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(+)-Muscarine has been synthesized from (S)-(-)-5-hydroxy-2(5H)-furanone via rather a long pathway to provide easy access to a wide variety of its analogues. (C) 2000 Published by Elsevier Science Ltd.
- Kyung Ho Kang,Mi Young Cha,Ae Nim Pae,Kyung Il Choi,Yong Seo Cho,Hun Yeong Koh,Bong Young Chung
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p. 8137 - 8140
(2007/10/03)
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- Chiral synthesis of (S)-(+)-γ-hydroxymethyl-γ-butyrolactone
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S-(+)-γ-hydroxymethyl-γ-butyrolactone has been synthesized from D- ribonolactone as chiral template.
- Salas-Reyes
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p. 2187 - 2199
(2007/10/03)
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- A synthetic route to 3-C-alkyl (or 3-C-phenyl-) 2,3-dideoxy-D-erythro- pentono-1,4-lactones: Intermediates in the synthesis of 2(3H)-furanones
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A series of 3-C-alkyl- (and 3-C-phenyl-) 2,3-dideoxy-D-erythro-pentono- 1,4-lactones, compounds which are important in the synthesis of modified nucleosides and antibiotic sugars, were synthesized from D-ribonolactone. By a route that proceeded via 5-O-pr
- Raveendranath,Blazis,Agyei-Aye,Hebbler,Gentile,Hawkins,Johnson,Baker
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p. 207 - 223
(2007/10/02)
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- Vitamin C and Isovitamin C Derived Chemistry. 3. Chiral Butenolides via Efficient 2,3-Didehydroxylations of L-Gulono-, D-Mannono-, and D-Ribono-1,4-lactones
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Efficient, operationally simple procedures for preparing the chiral butenolides 3a, 4a, 13a,b, and 16a-d from the commercial L-ascorbic acid (L-threo-hex-2-enono-1,4-lactone) and D-isoascorbic acid (D-erythro-hex-2-eno-no-1,4-lactone) are described.The concept centers on the novel NaHSO3-induced regiospecific trans-β-bromo-acetoxy elimination of the readily accessible O-acetylated bromodeoxyaldono-1,4-lactones 10a,b to compounds 13a,b.These, on deacetylation and treatment of the resulting bromohydrins 16a,b with Ag2O, afford the enantiomerically pure epoxides 16c,d and thence, in boiling water, the corresponding diols 3a and 4a.In a similar manner NaHSO3 causes the D-ribono-1,4-lactone-derived bromo acetate mixture 17a,b to undergo elimination to the corresponding butenolides 18a,b, which, on subsequent hydrolysis and chromatographic purification, has given compound 1a in 48percent overall yield.
- Vekemans, Josef A. J. M.,Franken, Gabriel A. M.,Dapperens, Cornelis W. M.,Godefroi, Erik F.,Chittenden, Gordon J. F.
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p. 627 - 633
(2007/10/02)
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- A Short Synthesis of (S)-5-Hydroxy-2-penten-4-olide from D-Mannitol via 2,3-O-Isopropylidene-D-glyceraldehyde
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(S)-5-Hydroxy-2-penten-4-olide (5) was synthesized in three steps starting from D-mannitol bis(acetonide) (1), via D-glyceraldehyde acetonide (2) by Z-selective Wittig reaction, acid-catalyzed lactonization and crystallization with a total yield of 40percent.
- Haefele, Brigitte,Jaeger, Volker
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- ASYMMETRIC TOTAL SYNTHESIS OF NATURAL (-)- AND UNNATURAL (+)-STEGANACIN DETERMINATION OF THE ABSOLUTE CONFIGURATION OF NATURAL ANTITUMOR STEGANACIN
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A virtually complete asymmetric control in the synthesis of 2,3-disubstituted butan-4-olide (10) was demonstrated by employing the butenolide (12) as the chiral acceptor for the conjugate 1,4-addition.Highly efficient asymmetric total synthesis of natural (-)- and unnatural (+)-steganacin was accomplished.The absolute stereostructure of natural antitumor steganacin was determined to be 1.
- Tomioka, Kiyoshi,Ishiguro, Tsuneo,Iitaka, Yoichi,Koga, Kenji
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p. 1303 - 1312
(2007/10/02)
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- STUDIES ON STRUCTURALLY SIMPLE α,β-BUTENOLIDES-II (-)-(S)-γ-HYDROXYMETHYL-α,β-BUTENOLIDE AND DERIVATIVES FROM D-RIBONOLACTONE EFFICIENT SYNTHESIS OF (-)-RANUNCULIN
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A short synthesis of the title compound, 16, from D-ribonolactone is described.Two alternative approaches differing in the timing of the C=C double bond creation are used to prepare some chiral derivatives of 16. (-)-Ranunculin, a glycoside present in Ranunculaceae, has been synthetized for the first time.
- Camps, P.,Cardellach, J.,Font, J.,Ortuno, R. M.,Ponsati, O
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p. 2395 - 2402
(2007/10/02)
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- SYNTHETIC APPROACHES TOWARD VERRUCARIN A. CHIRAL SYNTHESIS OF (-)-VERRUCARINOLACTONE
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(-)-Verrucarinolactone ((2S,3R)-2,5-dihydroxy-3-methylvaleric acid δ-lactone) (4) was synthesized stereoselectively from an optically active butyrolactone ((S)-γ-trityloxymethyl-γ-butyrolactone) (6) as a chiral synthon.
- Tomioka, Kiyoshi,Sato, Fuminori,Koga, Kenji
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p. 311 - 316
(2007/10/02)
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- A SHORT SYNTHESYS OF (S)-5-HYDROXYMETHYL-(5H)-FURAN-2-ONE AND DERIVATIVES FROM D-RIBONOLACTONE
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We describe a short synthesis of (S)-5-hydroxymethyl-(5H)-furan-2-one and some 5-O-derivatives, which are being used as key starting products for the synthesis of several antileukaemic lignan lactones, from D-ribonolactone.
- Camps, P.,Font, J.,Ponsati, O.
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p. 1471 - 1472
(2007/10/02)
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- FIRST ASYMMETRIC TOTAL SYNTHESIS OF (+)-STEGANACIN. DETERMINATION OF ABSOLUTE STEREOCHEMISTRY
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(+)-Steganacin was synthesized in a new and highly specific asymmetric pathway based on the novel application of chiral γ-lactone as a chiral synthon.By this synthesis the absolute stereochemistry of natural (-)-steganacin could be determined in unequivoc
- Tomioka, Kiyoshi,Ishiguru, Tsuneo,Koga, Kenji
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p. 2973 - 2976
(2007/10/02)
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