A new and expeditious entry to 7-oxabicyclo[3.2.1]octan-8-ol and 2- oxabicyclo[3.3.1]nonan-9-ol skeletons via intramolecular Michael addition- S(N)2' ring opening of 7-oxabicyclic sulfones

Tetrahedron Letters

Volumn 41, Issue 15, 2000, Pages 2549-2551

  Aceña, José Luis ^a   Arjona, Odón ^a   Mañas, Rosa ^a   Plumet, Joaquín ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

7 oxabicyclo 2.2.1 heptane; Intramolecular Michael addition; Natural products; Ring opening

Indexed keywords

BICYCLO COMPOUND; CYCLOHEXENE DERIVATIVE; NATURAL PRODUCT;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0034620950     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00226-4     Document Type: Article

References (11)

1. A search in the Dictionary of Natural Products on CD-ROM, Chapman and Hall/CRCnet BASE Version 8.1, August 1999, gives 33 references of natural products with the subunit 2 and more than 500 references of natural products with the subunit 1.
2. Arjona, O.; de Dios, A.; de la Pradilla, R. F.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 3906-3916.
3. For selected and recent references, see: (a) Arjona, O.; Menchaca, R.; Plumet, J. Tetrahedron Lett. 1998, 39, 6753-6756.
4. (b) Arjona, O.; Iradier, F.; Plumet, J.; Martínez, M. P.; Cano, F. H.; Fonseca, I. Tetrahedron Lett. 1998, 39, 6741-6744.
5. (c) Arjona, O.; Borrallo, C.; Iradier, F.; Medel, R.; Plumet, J. Tetrahedron Lett. 1998, 39, 1977-1980.
6. To the best of our knowledge only a very few isolated cases of intramolecular nucleophilic ring openings of oxanorbornenic compounds have been previously reported, see: (a) Lautens, M.; Kumanovic, S. J. Am. Chem. Soc. 1995, 117, 1954-1964.
7. (b) Lautens, M.; Fillion, E. J. Org. Chem. 1998, 63, 647-656.
8. The synthetic versatility of the vinylsulfone functionality is well documented in the literature. See: (a) Simpkins, N. S. In Sulfones in Organic Synthesis: Tetrahedron Organic Chemistry Series, Vol. 10; Pergamon Press: Oxford, 1993.
9. (b) Najera, C.; Yus, M. Tetrahedron 1999, 55, 10 547-10 658.
10. (a) Ogawa, S.; Iwasawa, Y.; Nose, T.; Suami, T.; Ohba, S.; Ito, M.; Saito, Y. J. Chem. Soc., Perkin Trans. 1 1985, 903-906.
11. (b) Vieira, E.; Vogel, P. Helv. Chim. Acta 1983, 66, 1865-1871.