Enantio- and diastereoselective synthesis of erysulfone and erysulfoxide

Tetrahedron Letters

Volumn 38, Issue 52, 1997, Pages 9081-9084

  Bourdeau, Laurence ^a   Sutherland, Alan G ^a,b  

^a LONDON METROPOLITAN UNIVERSITY   (United Kingdom)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NATURAL PRODUCT; PLANT EXTRACT;

ARTICLE; CHIRALITY; CONTROLLED STUDY; DIASTEREOISOMER; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0030733982     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10440-3     Document Type: Article

References (13)

1. Piatak, D.M.; Tang, P.-F.L.; Sorensen, P.D.; J. Nat. Prod., 1985, 48, 424-428.
2. Piatak, D.M.; Tang, P.-F.L.; Franciskovich, J.; Rogers, R.D. J. Nat. Prod., 1991, 54, 9002-904.
3. Ribbons, D.W.; Sutherland, A.G. Tetrahedron, 1994, 50, 3587-3594.
4. a) Avigad, G.; Englard, S. Fed. Proc. Fed. Am. Soc. Exp. Biol., 1969, 28, 345.
5. b) Note than many papers in this area employ a butenolide numbering system, where the chiral centre is at the 4-position.
6. Quinoa, E.; Kho, E.; Manes, L.V.; Crews, P.; Bakus, G.J. J. Org. Chem., 1986, 51, 4260-4264.
7. Bloch, R.; Seck, M. Tetrahedron Lett., 1987, 28, 5819-5820.
8. Gawronski, J.K.; van Oeveren, A.; van der Deen, H.; Leung, C.H.; Feringa, B.L. J. Org. Chem., 1996, 61, 1513-1515.
9. Ghosh, S.K.; Chattopadhyay, S.; Mamdapur, V.R. Tetrahedron, 1991, 47, 3089-3094.
10. Note that in this synthetic sequence, (5S)-muconolactone will give (5R)-erysulfone.
11. Zhao, S.H.; Samuel, O.; Kagan, H.B. Tetrahedron, 1987, 43, 5135-5144.
12. Westwell, A.D.; Thornton-Pett, M.; Rayner, C.M. J. Chem. Soc., Perkin Trans, I, 1995, 847-859.
13. We were able to determine the relative amount of the two diastereomeric sulfoxides by integration of the peaks corresponding to the methyl groups in the 1H NMR spectrum: the S sulfoxide methyl group appeared at 2.63 ppm, that of the diastereoisomer at 2.61.