An expedient synthesis of (R)-(+)-umbelactone

Tetrahedron Asymmetry

Volumn 7, Issue 5, 1996, Pages 1281-1284

  Gibson, Colin L ^a   Handa, Sheetal ^b  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 FURANONE DERIVATIVE; UMBELACTONE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029937055     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00144-9     Document Type: Article

References (12)

1. Agarwal, S. K.; Rastogi, R. P. Phytochemistry, 1978, 17, 1663.
2. Dhar, M. L.; Dhar, M. M.; Dhawan, B. N.; Mehrotra, B. N.; Ray, C. Indian J. Exp. Biol., 1968, 6, 241.
3. Caine, D.; Frobese, S.; Ukachukwu, V. C. J. Org. Chem., 1983, 48, 740.
4. Ortuña, R. M.; Bigorra, J. Font, J. Tetrahedron, 1987, 43, 2199.
5. Sato, T.; Okumura, Y.; Itai, J.; Fujisawa, T. Chem. Lett., 1988, 1537.
6. The (S)-acid 2 was available enantiomerically pure in useful quantities (> 100 g) from Shell Research Ltd., Shell Research Centre, Sittingbourne, Kent, ME9 8AG, UK.
7. 3).
8. Direct reaction of the (S)-acid 2 with methyl lithium provides the (S)-ketone 4 in poor yield (40%); Handa, S; Hawes, J. E.; Pryce, R. J. Synth. Commun., 1995, 25, 2837.
9. Still, W. C.; Gennari, C. Tetrahedron Lett., 1983, 24, 4405
10. Beckmann, M.; Hildebrandt, H.; Winterfeldt, E, Tetrahedron: Asymm., 1990, 1, 335.
11. Unsaturated (E)-amides have been isomerized to the (Z)-amides under these conditions: Crombie, L.; Taylor, L, J. Chem. Soc., 1957, 2761.
12. γ-Hydroxy α,β-unsaturated esters have been isomerized to 2(5H)-furanones under these conditions: Epstein, W. W.; Sonntag, A. C., J. Org. Chem., 1967, 32, 3390.