Strategies for the synthesis of enantiomerically pure medium-sized carbocycles from carbohydrates

Journal of Carbohydrate Chemistry

Volumn 21, Issue 3, 2002, Pages 201-218

  Marco Contelles, José ^a   De Opazo, Elsa ^a  

^a CSIC   (Spain)

Author keywords

1,3 Dipolar cycloaddition reaction; Carbocyclization; Carbohydrates; Medium sized carbocycles; Nitrones; Pauson Khand reaction

Indexed keywords

1,7,8 TRIDEOXY 2 O METHYL 1 [OXIDO(PHENYLMETHYL)IMINO] 3,6 BIS O (PHENYLMETHYL) DEXTRO GLYCERO DEXTRO MANNOOCT 7 ENITOL; 1,7,8 TRIDEOXY 2,4,5 TRI O METHYL 1 [OXIDO(PHENYLMETHYL)IMINO] 3,6 BIS O (PHENYLMETHYL) DEXTRO GLYCERO DEXTRO MANNOOCT 7 ENITOL; BICYCLO COMPOUND; CARBOHYDRATE DERIVATIVE; DIDEOXY 3,4:5,6 BIS O (1 METHYLETHYLIDENE) DEXTRO GLYCERO DEXTRO GLUCONON 1 EN 8 YNITOL; ISOXAZOLE DERIVATIVE; MANNOSE; NITRONE DERIVATIVE; OCTAHYDRO 9 METHOXY 6,6 DIMETHYL 4,8 BIS(PHENYLMETHYL) 1H [1,3]DIOXOLO[4,5]CYCLOHEP[1,2 C]ISOXAZOLE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; CYCLOADDITION; ENANTIOMER; ENTROPY; METHODOLOGY; PRECURSOR; SPECIES; TRANS ISOMER;

EID: 0036395669     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-120004333     Document Type: Article

References (52)

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50. The importance of pre-existing heterocycles in selected positions and orientations on acyclic precursors for successful carbocyclization processes has been demostrated in our laboratory: a) Marco-Contelles, J.; Ruiz, P.; Martínez, L.; Martínez-Grau, A. Strategies and tactics for free radical carbocyclization: synthesis of polyfunctionalized cyclopentanoid molecules from carbohydrates. Tetrahedron 1993, 49, 6669-6694; b) Marco-Contelles, J.; Bernabé, M.; Ayala, D.; Sánchez, B. 6-endo-dig free radical carbocyclizations: a new strategy for the synthesis of cyclitols. J. Org. Chem. 1994, 59, 1234-1235. For an application of the results reported in this paper, see: c) Gómez, A.M.; Danelón, G.O.; Valverde, S.; López, J.C. Regio- and stereocontrolled 6-endo-trig radical cyclization of vinyl radicals: a novel entry to carbasugars from carbohydrates. J. Org. Chem. 1998, 63, 9626-9627 (Corrigendum: J. Org. Chem. 1999, 64, 7280).
51. The importance of pre-existing heterocycles in selected positions and orientations on acyclic precursors for successful carbocyclization processes has been demostrated in our laboratory: a) Marco-Contelles, J.; Ruiz, P.; Martínez, L.; Martínez-Grau, A. Strategies and tactics for free radical carbocyclization: synthesis of polyfunctionalized cyclopentanoid molecules from carbohydrates. Tetrahedron 1993, 49, 6669-6694; b) Marco-Contelles, J.; Bernabé, M.; Ayala, D.; Sánchez, B. 6-endo-dig free radical carbocyclizations: a new strategy for the synthesis of cyclitols. J. Org. Chem. 1994, 59, 1234-1235. For an application of the results reported in this paper, see: c) Gómez, A.M.; Danelón, G.O.; Valverde, S.; López, J.C. Regio- and stereocontrolled 6-endo-trig radical cyclization of vinyl radicals: a novel entry to carbasugars from carbohydrates. J. Org. Chem. 1998, 63, 9626-9627 (Corrigendum: J. Org. Chem. 1999, 64, 7280).
52. The importance of pre-existing heterocycles in selected positions and orientations on acyclic precursors for successful carbocyclization processes has been demostrated in our laboratory: a) Marco-Contelles, J.; Ruiz, P.; Martínez, L.; Martínez-Grau, A. Strategies and tactics for free radical carbocyclization: synthesis of polyfunctionalized cyclopentanoid molecules from carbohydrates. Tetrahedron 1993, 49, 6669-6694; b) Marco-Contelles, J.; Bernabé, M.; Ayala, D.; Sánchez, B. 6-endo-dig free radical carbocyclizations: a new strategy for the synthesis of cyclitols. J. Org. Chem. 1994, 59, 1234-1235. For an application of the results reported in this paper, see: c) Gómez, A.M.; Danelón, G.O.; Valverde, S.; López, J.C. Regio- and stereocontrolled 6-endo-trig radical cyclization of vinyl radicals: a novel entry to carbasugars from carbohydrates. J. Org. Chem. 1998, 63, 9626-9627 (Corrigendum: J. Org. Chem. 1999, 64, 7280).