Efficient syntheses of protected (2s,3s)-2,3-bis(hydroxymethyl)cyclobutanone, key intermediates for the synthesis of chiral carbocyclic analogues of oxetanocin

Hsiao, Chi-Nung; Hannick, Steven M.

doi:10.1016/s0040-4039(00)97127-2

Cited by 45 publications

(15 citation statements)

References 17 publications

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“…In fact, exposure of a single diastereomer of diethyl amide 206 to deuterated diisopropylamine led to no deuterium incorporation, which is suggestive of no epimerization of that center over 4 h. The reaction of spiroepoxy-β-lactone 202 with water over prolonged periods of time led to α-hydroxy ketone 204 . Mechanistically, there are two routes that could provide the same ketone product and in this instance, use of heavy water, H 2 O18, served to unequivocally infer the mechanism followed. The results indicate, not unexpectedly, that nucleophilic attack of water occurs exclusively at C2 leading to ketone 204 in analogy to several related systems described above.…”

Section: 14-dioxaspiro[23]hexan-5-onesmentioning

confidence: 98%

“…The initial application of oxaspiro[2.2]pentanes was toward the synthesis of carbocyclic analogues of oxetanocin, an antibiotic/antiviral natural product (Scheme 5). 18 Hsiao’s synthesis hinges on the construction of an optically active cyclobutanone 15 . Their approach to this ring system depended on the preparation of oxaspiro[2.2]pentane 14 and the subsequent rearrangement to cyclobutanone 15 .…”

Section: Oxaspiro[22]pentanesmentioning

confidence: 99%

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Synthesis of unusually strained spiroheterocyclic ring systems and their exploits in synthesis

2009

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Section: 14-dioxaspiro[23]hexan-5-onesmentioning

confidence: 98%

Section: Oxaspiro[22]pentanesmentioning

confidence: 99%

Synthesis of unusually strained spiroheterocyclic ring systems and their exploits in synthesis

2009

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“…The chiral Feist's acid 141, obtained by chemical resolution of the enantiomeric mixture 140 via fractional crystallization of the quinine acid salt [66], was used as starting material for the synthesis of the key intermediate cyclobutanones 117, 146, and others (Scheme 19) [67]. The cyclopropyl-cyclobutyl conversion was achieved by epoxidation of the exocyclic double bond followed by lithium iodidecatalyzed ring rearrangement of the spiro intermediate 145.…”

Section: Cyclobutyl Nucleosidesmentioning

confidence: 99%

Chiral Synthesis of Carbocyclic Nucleoside Analogs from Noncarbohydrate Precursors

Casu¹,

Chiacchio²,

Romeo³

et al. 2007

COC

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Nucleosides represent a very important group of molecules, both chemically and biologically. Over the past forty years, the continued success of nucleoside analogs as chemotherapeutic agents has been both the result of and the driving force for the development of new synthetic methodologies to access analogs that may differ considerably from natural nucleosides. Among the many classes of nucleoside analogs that have been prepared and evaluated, carbocyclic nucleosides featured diverse and challenging syntheses and interesting biological activity. Carbohydrate chemistry has been elegantly and thoroughly exploited for the synthesis of carbocyclic nucleoside analogs, thanks to the availability and versatility of highly functionalized chiral precursors. In a number of examples, however, the synthesis of carbocyclic nucleosides has been elegantly and efficiently achieved from non-carbohydrate starting materials, either from natural optically active molecules, via chemical or enzymatic desymmetrization of prochiral molecules, or resolution of racemates. This review will discuss chiral syntheses of carbocyclic nucleoside analogs from non-carbohydrate precursors. O X HO B 2',3'-Dideoxy (d2N) HO HO B HO B X Y Carbocyclic X O HO B Heterosubstituted X HO B Y Acyclic O HO B 2',3'-Didehydro-2',3'-dideoxy (d4N) O HO HO B OH

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“…Abott's group described the synthesis of optically active cyclobutanone 165, applying the transformation reaction of oxaspiropentane compound to cyclobutanone with catalytic lithium iodide. 38…”

Section: Abbott's Synthesis (I)mentioning

confidence: 99%

Syntheses of Oxetanocin A and Related Unusual Nucleosides with Bis(hydroxymethyl)-branched Sugars

Ichikawa¹,

Kato²

2004

Synthesis

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Since the naturally occurring unusual nucleoside oxetanocin A and its derivatives have been found to be effective as anti-HIV-1 and anti-herpes virus agents in 1986, the syntheses of different types of sugar-modified nucleoside analogs have been reported. In this review we will give an overview of the efforts to synthesize oxetanocin A from the first synthesis in 1987 and the related unusual nucleosides with bis(hydroxymethyl)-branched sugars, including our works in this area. 7Thietanosyl Nucleosides

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Efficient syntheses of protected (2s,3s)-2,3-bis(hydroxymethyl)cyclobutanone, key intermediates for the synthesis of chiral carbocyclic analogues of oxetanocin

Cited by 45 publications

References 17 publications

Synthesis of unusually strained spiroheterocyclic ring systems and their exploits in synthesis

Synthesis of unusually strained spiroheterocyclic ring systems and their exploits in synthesis

Chiral Synthesis of Carbocyclic Nucleoside Analogs from Noncarbohydrate Precursors

Syntheses of Oxetanocin A and Related Unusual Nucleosides with Bis(hydroxymethyl)-branched Sugars

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