An efficient synthesis of 2-aryl and 2-alkenyl-3-alkoxy-cyclohexenones by a modified stille reaction

Tetrahedron Letters

Volumn 40, Issue 3, 1999, Pages 459-462

  Furness, M Scott ^a   Robinson, T Philip ^a   Goldsmith, David J ^a,b   Bowen, J Phillip ^a  

^a UNIVERSITY OF GEORGIA   (United States)

^b EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE DERIVATIVE; 2 PHENYL 3 METHOXY 2 CYCLOHEXENONE; ANGIOGENESIS INHIBITOR; FUMAGILIN; UNCLASSIFIED DRUG;

ANGIOGENESIS; ARTICLE; BINDING KINETICS; BROMINATION; CHEMICAL REACTION KINETICS; CROSS REACTION; DRUG SYNTHESIS; PROTEIN MODIFICATION; STEREOCHEMISTRY;

EID: 0033555239     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02424-1     Document Type: Article

References (12)

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4. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
5. Suzuki, A. Acc. Chem. Res. 1982, 15, 178.
6. Stille, J. K. Angew. Chem. Int. Ed. Engl. 1986, 25, 508.
7. Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5518.
8. Dieck, H. A.; Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133.
9. Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W. Tetrahedron Lett. 1992, 33, 919.
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11. 2: C, 71.03%; H, 7.95%; O, 21.03%. Found: C, 71.10%; H, 7.92%; O, 20.98%.
12. While attempting to apply the Heck reaction to our system (Scheme 3), we transferred the successful conditions described in this account to the simple olefin methyl acrylate. None of the desired coupled product was isolated, which suggests that the vinyl stannanes are necessary for coupling with α-bromo-β-methoxy enones.