Synthesis of α-pyrones via palladium-catalyzed annulation of internal alkynes

Tetrahedron Letters

Volumn 39, Issue 32, 1998, Pages 5713-5716

  Larock, Richard C ^a   Han, Xiaojun ^a   Doty, Mark J ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

Annulation; Halo esters; Palladium and compounds; Pyrones

Indexed keywords

2 PYRONE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG; VINYLIC BROMIDE; VINYLIC IODIDE; VINYLIC TRIFLATE;

ARTICLE; CATALYST; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; METAL BINDING; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; VIRUS INHIBITION;

EID: 0032491016     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01182-4     Document Type: Article

References (11)

1. [1] (a) Kvita V, Fischer W. Chimia 1992;46:457.
2. (b) Kvita V, Fischer W. Chimia 1993;47:3.
3. (c) Posner GH, Nelson T, Kinter C, Johnson N. J. Org. Chem. 1992;57:4083.
4. [2] Dickinson J. Nat. Prod. Rep. 1993;10:71.
5. [3] Vara Prasad JVN, Para KS, Lunney EA, Ortwine DF, Dunbar JB, Ferguson D, Tummino PJ, Hupe D, Tait BD, Domagala JM, Humblet C, Bhat TN, Liu B, Guerin DAM, Baldwin ET, Erickson JW, Sawyer TK. J. Am. Chem. Soc. 1994;116:6989.
6. [4] Larock RC, Yum EK, Doty MJ, Sham KC. J. Org. Chem. 1995;60:3270.
7. [5] Corey EJ, Gilman NW, Ganem BE. J. Am. Chem. Soc. 1968;90:5616.
8. [6] Duboudin JG, Jousseaume B. J. Organomet. Chem. 1979;168:1.
9. [7] Abad A, Arno M, Pedro JR, Seoane E. J. Chem. Soc., Perkin Trans. I 1983:2471.
10. [8] Keenan RM, Weinstock J, Finkelstein JA, Franz RG, Gaitanopoulos DE, Girard GR, Hill DT, Morgan TM, Samanen JM, Hempel J, Eggleston DS, Aiyar N, Griffin E, Ohlstein EH, Stack EJ, Weidley EF, Edwards R. J. Med. Chem. 1992;35:3858.
11. 4, and decanted. The solvent was evaporated under reduced pressure and the product was isolated by chromatography (EtOAc/hexanes) on a silica gel column.