A practical synthesis of enantiomerically pure (-)-geosmin via highly diastereoselective reduction of (4aS,8S)-4,4a,5,6,7,8-hexahydro-4a,8-dimethyl-2(3H)-naphthalenone

Tetrahedron Asymmetry

Volumn 7, Issue 10, 1996, Pages 2923-2928

  Saito, Akiko ^a   Tanaka, Akira ^a   Oritani, Takayuki ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GEOSMIN; NAPHTHALENE DERIVATIVE;

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

EID: 0030271768     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00383-7     Document Type: Article

References (12)

1. 1 Gerber N. N.; Lechevalier H. A. Appl. Microbiol. 1965, 13, 935.
2. 2 Ohloff G. in Progress in the Chemistry of Organic Natural Products, Eds. Herz W.; Grisebach H.; Kirby G. W.; Springer-Verlag: Wien, 1978, p. 483.
3. 3 Maga J. A. Food Rev. Int. 1987, 3, 269.
4. 4 Tanaka A.; Oritani T.; Uehara F.; Saito A.; Kishita H.; Niizeki Y.; Yokota H.; Fuchigami K. Wat.. Res. 1996, 30, 759.
5. 5 a) Marshall J. A.; Hochstetler A. R. J. Org. Chem. 1968, 33, 2593.
6. b) Ayer W. A.; Browne L. M.; Fung S. Can. J. Chem. 1976, 54, 3276.
7. c) Gosselin P.; Laurin P.; Rouessac F. Tetrahedron Lett. 1989, 30, 2775.
8. d) Revial G. Tetrahedron Lett. 1989, 30, 4121.
9. e) Kaiser R.; Nussbaumer C. Helv. Chim. Acta 1990, 73, 133.
10. 4 reduction has been converted to a stereochemically defined sesquiterpene lactone, frullanolide. See Petragnani N.; Ferraz H. M. C. Synthesis 1958, 27.
11. 7 Katritzky A. R.; Sengupta S. Tetrahedron Lett.. 1987, 28, 5419.
12. 8 A very expensive (±)-geosmin sample is available from Wako Pure Chemical Industries, Ltd.