Novel stereoselective addition of some nucleophiles to 2,3-bis(methylsulfanyl)norbornenobenzoquinone

Tetrahedron Letters

Volumn 38, Issue 15, 1997, Pages 2625-2628

  Wladislaw, Blanka ^a   Di Vitta, Claudio ^a   Marzorati, Liliana ^a   De Arruda Campos, Ivan P ^a,b   Lucchini, Vittorio ^c  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b PAULISTA UNIVERSITY   (Brazil)

^c CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE DERIVATIVE; NORBORNANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030937454     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00446-2     Document Type: Article

References (13)

1. Wladislaw, B.; Di Vitta, C.; Marzorati, L.; de Arruda Campos, I. P.; J. Chem. Research (S) 1994, 438.
2. 3): 6.86(2H, m), 4.09(2H, m), 2.63(6H, s), 2.28(2H, m).
3. Mehta, G.; Padma, S.; Karra, S. R.; Gopdas, K. R.; Cyr, D. R.; Das, P. K.; George, M. V.; J. Org. Chem. 1989, 54, 1342.
4. Wladislaw, B.; Marzorati, L.; Di Vitta, C.; Synthesis 1983, 464.
5. 1.
6. 4, 1 % at H7; H7 / 1 % at H8a.
7. 6), 1.60 (1H, m, H9s), 1.22 (1H, m, H9a);
8. 2 / 4 % at H8a.
9. 2Me); NOE experiments (irrad. on H / % of enhanc obs. on H′): H-N/ 1% at H9a and H9s; H9a and H9s/ 8 % at H8a.
10. 8a-9s) ring-junction protons are in accordance with those reported for the endo and exo 2,3-epoxides of some Diels-Alder adducts of 1,4-benzoquinones (Gates Jr., J. W.; O'Brien, D. D.; J. Org. Chem. 1965, 30, 2593; Youngquist, M. J.; O'Brien, D. F.; Gates Jr., J.W.; J.Am.Chem.Soc. 1966, 88, 4960; see also Marchand, A.P.; Methods Stereochem. Anal. 1982, 1, 1).
11. 8a-9s) ring-junction protons are in accordance with those reported for the endo and exo 2,3-epoxides of some Diels-Alder adducts of 1,4-benzoquinones (Gates Jr., J. W.; O'Brien, D. D.; J. Org. Chem. 1965, 30, 2593; Youngquist, M. J.; O'Brien, D. F.; Gates Jr., J.W.; J.Am.Chem.Soc. 1966, 88, 4960; see also Marchand, A.P.; Methods Stereochem. Anal. 1982, 1, 1).
12. 8a-9s) ring-junction protons are in accordance with those reported for the endo and exo 2,3-epoxides of some Diels-Alder adducts of 1,4-benzoquinones (Gates Jr., J. W.; O'Brien, D. D.; J. Org. Chem. 1965, 30, 2593; Youngquist, M. J.; O'Brien, D. F.; Gates Jr., J.W.; J.Am.Chem.Soc. 1966, 88, 4960; see also Marchand, A.P.; Methods Stereochem. Anal. 1982, 1, 1).
13. Oki, M.; Furakoshi, W.; Nakamura, A.; Bull.Chem.Soc. Japan 1971, 44, 828.