Toward a total synthesis of stigmatellin; An unproductive C-1'-C-2' disconnection

Tetrahedron Letters

Volumn 41, Issue 29, 2000, Pages 5495-5499

  Adje N ^a   Domon, L ^a   Vogeleisen Mutterer, F ^a   Uguen, D ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

STIGMATELLIN;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; PHOTOSYNTHESIS; POLYMERIZATION; STEREOISOMERISM; SYNTHESIS;

EID: 0034661874     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00813-3     Document Type: Article

References (11)

1. Höfle, G.; Kunze, B.; Zorzin, C.; Reichenbach, H. Liebigs Ann. Chem. 1984, 12, 1883-1904.
2. Oettmeier, W.; Goolde, D.; Kunze, B.; Höfle, G. Biochem. Biophys. Acta 1985, 106, 216-223.
3. Enders, J.; Osborn, S. J. Chem. Soc., Chem. Commun. 1993, 424-426.
4. Adjé, N.; Vogeleisen, F.; Uguen, D. Tetrahedron Lett. 1996, 37, 5893-5896.
5. Domon, L.; Uguen, D. Tetrahedron Lett. 2000, 41, 5501-5505.
6. (a) Julia, M.; Nel, A.; Righini, A.; Uguen, D. J. Organomet. Chem. 1983, 235, 113-120;
7. (b) Julia, M.; Nel, M.; Uguen, D. Bull. Soc. Chim. Fr. 1987, 487-492.
8. Presumably formed by basic elimination of an acetate ion in the transcient acetoxysulfone, followed by hydrogenation of the thus-formed vinylsulfone residue.
9. 2): 260.8 (0.85), 271.3 (0.9), 282.4 (0.69) (in bracket: ee values).
10. 3). Evaporation of the solvents was followed by chromatography of the residue on 60 silica gel (AcOEt) to afford the pure chromone.
11. 3 at 200 and 50 MHz, respectively.