Enantioselective Synthesis of γ,δ-Disubstituted β-Hydroxy δ-Lactones from Furans: Synthesis of (+)-Prelactone B and its C-4 Epimer

Synlett

Volumn , Issue 13, 2003, Pages 2092-2094

  Csákÿ, Aurelio G ^a   Mba, Myriam ^a   Plumet, Joaquín ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

Cyclopentenones; Furans; Lactones; Natural products; Stereoselective synthesis

Indexed keywords

4 HYDROXYCYCLOPENT 2 ENONE DERIVATIVE; 4 HYDROXYCYCLOPENTANONE DERIVATIVE; ALKANONE; BETA HYDROXY DELTA LACTONE DERIVATIVE; FURAN DERIVATIVE; LACTONE DERIVATIVE; PRELACTONE B; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHIRALITY; ENANTIOSELECTIVITY; EPIMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0242383405     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

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8. 3, 200 MHz) allowed for the determination of the ee values.
9. 3)) was determined by transformation into (+)-2 followed by Mosher's ester analysis. See text and ref. 7
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21. 3).
22. D = +40 (c 0.7, MeOH). The spectroscopical data are in agreement with those previously reported. See ref. 3b
23. 3): δ = 164.9, 151.8, 120.1, 87.7, 30.9, 29.1, 19.6, 16.3, 15.4 ppm.
24. The optical rotation of 1b was not determined. Extensive decomposition was observed upon attempted purification by chromatography on silica gel.
25. 3): δ = 175.3, 83.9, 68.0, 39.2, 34.6, 28.8, 19.7, 13.9, 13.3 ppm.
26. These transformations have been carried out at 50 mmol scale.