Synthesis of (-)-(1S,5R)- and (+)-(1R,5S)-trifluoroanalogues of frontalin

Tetrahedron Letters

Volumn 40, Issue 34, 1999, Pages 6317-6320

  Bravo, Pierfrancesco ^a   Corradi, Eleonora ^a   Frigerio, Massimo ^a   Meille, Stefano Valdo ^a   Panzeri, Walter ^b   Pesenti, Cristina ^a   Viani, Fiorenza ^b  

^a POLITECNICO DI MILANO   (Italy)

^b CNR   (Italy)

Author keywords

Diastereoselection; Epoxides; Sulfoxides; Trifluorofrontalin

Indexed keywords

FRONTALIN DERIVATIVE; PHEROMONE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 0033588358     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01186-7     Document Type: Article

References (14)

1. (a) D'Silva, T. D. J.; Peck, D. W. J. Org. Chem. 1972, 37, 1828-1829;
2. (b) Mori, K. Eur. J. Org. Chem. 1988, 1479-1489 and references cited therein.
3. For multigram synthesis of (-)-frontalin, see: (a) Nishimura, Y.; Mori, K. Eur. J. Org. Chem. 1998, 233-236;
4. (b) Chen, S.-T; Fang, J.-M. J. Org. Chem. 1997, 62, 4349-4357;
5. from asymmetric [3+2] cycloaddition, see: (c) Kouklovsky, C.; Dirat, O.; Berranger, T.; Langlois, Y.; Tran-Huu-Dau, M. E.; Riche, C. J. Org. Chem. 1988, 63, 5123-5128;
6. from chiral hydrazones, see: (d) Majewski, M.; Nowak, P. Tetrahedron: Asymmetry 1998, 9, 2611-2617;
7. from Sharpless asymmetric dihydroxylation reaction, see: (e) Taniguchi, T.; Nakamura, K.; Ogasawara, K. Synthesis 1997, 509-511;
8. for a chemoenzymatic approach, see: (f) Kroutil, W.; Osprian, I.; Mischitz, M.; Faber, K. Synthesis 1997, 156-158.
9. (a) Arnone, A.; Bravo, P.; Frigerio, M.; Viani, F.; Soloshonok, V. A. Tetrahedron 1998, 54, 11841-11860;
10. for the selective production of threo-epoxy compounds, see: (b) Ohashi, N.; Takamidai, T.; Fujimoto, K.; Tanaka, Y. Eur. Pat. 1991 Appl. EP 415,320 A2; C.A. 114:2471095.
11. Drabowicz, J.; Oae, S. Synthesis 1977, 404-405.
12. 3).
13. Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
14. Full X-ray diffraction data will be published in due course.