One pot michael addition, vinylsulfone isomerization and alkynyl to alkenyl triple bond reduction. Synthesis of a carbasugar related to Rancinamycin III

Tetrahedron Letters

Volumn 39, Issue 14, 1998, Pages 1977-1980

  Arjona, Odón ^a   Borrallo, Cristina ^a   Iradier, Fátima ^a   Medel, Rocío ^a   Plumet, Joaquín ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; RANCINAMYCIN III; SULFONE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; ISOMERISM; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 0032473850     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00109-9     Document Type: Article

References (9)

1. 1. a) Arjona, O.; de Dios, A.; Fernández de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 3906-3916.
2. b) Aceña, J. L.; Arjona, O.; Iradier, F.; Plumet, J. Tetrahedron Lett. 1996, 37, 105-106.
3. th Ed. John Wiley, 1992, pp. 582-583.
4. 3. This reaction pathway appears to be reminiscent of those proposed for organocopper reagents mediated 1,6-additions to alkenynones and alkenylnoates: Frederick, M. A.; Hulce, M.; Tetrahedron 1997, 53, 10197-10277. See pp. 10204-10206.
5. 4. Compounds 7 were prepared by Diels-Alder cycloaddition of 2-methoxyfuran and trans-1,2-bis(phenylsulfonyl)-ethylene followed by chemical elaboration of the resulting adducts. Full details wil be given elsewhere.
6. 5. a) Argoudelis, A. D.; Pike, T. R.; Sprague, R. W.; J. Antibiot. 1976, 29, 777-786.
7. b) Argoudelis, A. D.; Sprague, R. W.; Mizsak, S. A.; J. Antibiot. 1976, 29, 787-796.
8. 6. A 18 % yield of compound 13 has been found in bishydroxylation of compound 3.
9. 1H-RMN, selective decoupling experiments were used for stereochemical determination. (formula presented)