A unified strategy for the synthesis of enantiomerically pure branched-chain cyclohexenones and -cyclopentenones from a single progenitor

Tetrahedron Letters

Volumn 38, Issue 34, 1997, Pages 5977-5980

  Chretien F ^a   Khaldi, M ^a   Chapleur, Y ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; 2 CYCLOHEXENONE DERIVATIVE; CYCLOHEXENE DERIVATIVE; CYCLOPENTENONE DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0343145720     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01348-8     Document Type: Article

References (20)

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16. This condensation has been also applied to 2,3:5,6-di-O-isopropylidene-D-mannono-l,4-lactone, 5,6-O-isopropylidene-2,3-di-O-trimethylsilyl-D-galactono-1,4-lactone and 2,3-O-isopropylidene-D-ribono-1,4-lactone in 50, 20 and 55 % yield respectively. In the latter case a two fold excess of lithium enolate was used to deprotonate the free 5-OH group.
17. 2), 142.3 (C-5), 155.4 (C-4), 162.6 (C=O), 199.1 (C=O).
18. No other diastereoisomer which may result from epimerisation of the intermediate keto-aldehyde was detected in the reaction mixture.
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