Synthesis of natural products possessing a benzo[b]furan skeleton

Tetrahedron Letters

Volumn 39, Issue 36, 1998, Pages 6581-6584

  Lütjens, Henning ^a   Scammells, Peter J ^a  

^a DEAKIN UNIVERSITY   (Australia)

Author keywords

Ailanthoidol; Benzo b furan; XH 14

Indexed keywords

2 (4 HYDROXY 3 METHOXYPHENYL) 5 (3 HYDROXYPROPYL) 7 METHOXY 3 BENZO[B]FURANCARBALDEHYDE; ADENOSINE A1 RECEPTOR ANTAGONIST; AILANTHINONE; AILANTHOIDOL; BENZOFURAN DERIVATIVE; CARBON MONOXIDE; CARBONYL DERIVATIVE; EUGENOL; FORMIC ACID; NATURAL PRODUCT; PALLADIUM; SALVIA MILTIORRHIZA EXTRACT; UNCLASSIFIED DRUG; VANILLIN;

ACYLATION; ARTICLE; CATALYST; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; NONHUMAN; STEREOCHEMISTRY; TRADITIONAL MEDICINE; TREE;

SALVIA MILTIORRHIZA;

EID: 0032171538     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01371-9     Document Type: Article

References (10)

1. [1] Belardinelli L, Shryock JC, Zhang Y, Scammells PJ, Olsson RA, Denis D, Milner P. Pfister J, Baker SP, J. Pharmacol. Exp. Ther. 1995;275:1167-1176.
2. [2] Yang Z, Hon MH, Chui KY, Xu HM, Lee CM, Cui YX, Wong HNC, Poon CD, Fung BM, Tetrahedron Lett. 1991;32:2061.
3. [3] Yang Z, Liu HB, Lee CM, Chang HM, Wong HNC, J. Org. Chem. 1992;57:7248.
4. [4] Sheen WS, Tsai IL, Teng CM, Chen IS, Phytochemistry, 1994;36:213.
5. [5] Hutchinson SA, Lütjens H, Scammells PJ, Bioorg. Med. Chem. Lett. 1997;7:3081-3084.
6. [6] Scammells PJ, Baker SP, Beauglehole AR, Bioorg. Med. Chem. 1998: in press.
7. [7] Kuo YH, Wu CH. J. Nat. Prod. 1996;59:625.
8. [8] Sonogashira K.: Coupling reactions between sp2 and sp carbon centres. In: Trost BM, editor. Comprehensive organic synthesis. New York: Pergamon Press, 1991;3:521.
9. [9] Kondo Y, Shiga F, Murata N, Sakamoto T, Yamanaka H. Tetrahedron, 1994;50:11803.
10. 2O (340 mg, 1.99 mmol) and sodium acetate (165 mg, 2.01 mmol) were stirred in methanol under an atmosphere of carbon monoxide for five hours. Normal workup followed by purification by column chromatography (hexanes-chloroform-ethyl acetate 5:5:1) afforded the benzofuran 9 (332 mg, 0,64 mmol, 68%). The unfunctionalized benzofuran 10 (140 mg) was obtained as a by-product.