A stereoselective one-pot synthesis of perhydro-7a-hydroxy-7-phenylthiofurano[3,2-b]pyran via an acid-catalysed deprotection/double cyclisation/rearrangement sequence

Tetrahedron Letters

Volumn 39, Issue 21, 1998, Pages 3605-3608

  Edwards, Neil ^a   Macritchie, Jacqueline A ^b   Parsons, Philip J ^a  

^a UNIVERSITY OF SUSSEX   (United Kingdom)

^b AgrEvo UK Limited   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; ETHER DERIVATIVE; HALICHONDRIN B;

ARTICLE; CATALYSIS; CONFORMATIONAL TRANSITION; CYCLIZATION; DEHYDRATION; PROTON TRANSPORT; REACTION ANALYSIS; SYNTHESIS; THERMODYNAMICS;

EID: 0032555029     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00560-7     Document Type: Article

References (14)

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2. Fukuzawa, A.; Kurosawa, E.; Irie, T. Tetrahedron Lett. 1972, 3
3. (a) Binch, H.M.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1996, 401;
4. (b) Newcombe, N.J.; Mahon, M.F.; Molloy, K.C.; Alker, D.; Gallagher, T. J. Am. Chem. Soc. 1993, 115, 6430
5. Oishi, T.; Nagumo, Y.; Hirama, M. Synlett 1997, 980
6. (a) Nicolaou, K.C.; Postema, M.H.D.; Claiborne, C.F. J. Am. Chem. Soc. 1996, 118, 1565;
7. (b) Nicolaou, K.C.; Postema, M.H.D.; Yue, E.W.; Nadin, A. J. Am. Chem. Soc. 1996, 118, 10335
8. Pairaudeau, G.; Parsons, P.J.; Underwood, J.M. J. Chem. Soc., Chem. Commun. 1987, 1718
9. 3, ppm) 1.63 (1H, dddd, J=1.8, 1.8, 4.9, 13.4 Hz); 1.78 (1H, ddd, J=2.4, 7.5, 13.0 Hz); 2.00 (1H, dddd, J=4.2, 12.5, 12.5, 13.4 Hz); 2.22-2.31 (1H, m); 3.01 (1H, ddd, J=1.8, 11.5, 12.5 Hz); 3.22 (1H, dd, J=4.9, 12.5 Hz); 3.30 (1H, s); 3.60 (1H, ddd, J=1.8, 4.2, 11.5 Hz); 3.74 (1H, d, J=4.4 Hz); 3.96 (1H, ddd, J=2.2, 7.7, 9.9 Hz); 4.05 (1H, m); 7.00-7.41 (5H, m)
10. Corey, E.J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190
11. Prepared from 3-buten-1-ol by silylation (ref. 8) followed by ozonolysis.
12. Barrett, A.G.M.; Dhanak, D.; Grabowski, G.G.; Taylor, S.J. Org. Synth. 1990, 68, 8
13. Using Cache Satellite Version 3.0. © 1997 Oxford Molecular Ltd.
14. 3a,3′≈90°, in agreement with the analysis of the observed NMR spectrum.