Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2007(6): 873-882
DOI: 10.1055/s-2007-965939
DOI: 10.1055/s-2007-965939
PAPER
© Georg Thieme Verlag Stuttgart · New York
Palladium-Catalyzed Synthesis of Lipophilic Benzo[b]furans from Cardanol
Further Information
Received
29 November 2006
Publication Date:
20 February 2007 (online)
Publication History
Publication Date:
20 February 2007 (online)
Abstract
o-Iodocardanol, readily available from cardanol by iodination, has been used to prepare a variety of lipophilic benzo[b]furans. 2-Substituted benzo[b]furans have been prepared by a Sonogashira cross-coupling/cyclization process. 2,3-Disubstituted benzo[b]furans have been obtained from o-alkynylcardanols by an oxypalladation/reductive elimination process.
Key words
cross-coupling - cyclization - alkynes - benzo[b]furans - catalysis
- 1
Horton DA.Bourne GT.Smythe ML. Chem. Rev. 2003, 103: 893 -
2a
Judd DB.Dowle MD.Middlemiss D.Scopes DLC.Ross BC.Jack TL.Pass M.Tranquillini E.Hobson JE.Panchal TA.Stuart PG.Paton JMS.Hubbard T.Hilditch A.Drew GM.Robertson MJ.Clark KL.Travers A.Hunt AAE.Polley J.Eddershaw PJ.Bayliss MK.Manchee GR.Donnelly MD.Walker DG.Richards SA. J. Med. Chem. 1994, 37: 3108 -
2b
Kiyama R.Homna T.Hayashi K.Ogawa M.Hara M.Fujimoto M.Fujishita T. J. Med. Chem. 1995, 38: 2728 -
2c
Yoo S.Kim S.-K.Lee S.-H.Kim N.-J.Lee D.-W. Bioorg. Med. Chem. 2000, 8: 2311 -
3a
Gangjee A.Devraj R.McGuire JJ.Kisliuk RL. J. Med. Chem. 1995, 38: 3798 -
3b
Gangjee A.Devraj R.McGuire JJ.Kisliuk RL. J. Med. Chem. 1995, 38: 4495 -
3c
Hennequin LFA. inventors; WO 2003047585. ; Chem. Abstr. 2003, 139, 36448 -
3d
Helesbeux JJ.Duval O.Seraphin D.Roussakis C.Richomme P. J. Enzyme Inhib. Med. Chem. 2003, 18: 159 -
3e
Hayakawa I.Shioya R.Agatsuma T.Furukawa H.Sugano Y. Bioorg. Med. Chem. Lett. 2004, 14: 3411 -
3f
Eberle M,Bachmann F,Strebel A,Roy S,Saha G,Sadhukhan SK,Saxena R, andSrivastava S. inventors; WO 2005061476. ; Chem. Abstr. 2005, 143, 115430 -
3g
Rida SM.El-Hawash SAM.Fahmy HTY.Hazza AA.El-Meligy MMM. Arch. Pharm. Res. 2006, 29: 16 -
4a
Gubin J.de Vogelaer H.Inion H.Houben C.Lucchetti J.Mahaux J.Rosseels G.Peiren M.Clinet M.Polster P.Chatelain P. J. Med. Chem. 1993, 36: 1425 -
4b
Kozikowsky AP.Ma D.Du L.Lewin NE.Blumberg PM. Farmaco 1995, 50: 425 -
4c
Kozikowsky AP.Ma D.Du L.Lewin NE.Blumberg PM. J. Am. Chem. Soc. 1995, 117: 6666 -
4d
Termin AP,Martinborough E,Zimmermann N,Cohen CJ, andGutierrez CD. inventors; WO 2006010008. ; Chem. Abstr. 2006, 144, 164278 - 5
Ohemeng KA.Apollina MA.Nguyen VN.Schwender CF.Singer M.Steber M.Ariseli J.Argentieri D.Hageman W. J. Med. Chem. 1994, 37: 3663 -
6a
Nagahara T.Yokoyama Y.Inamura K.Katakura S.Komoriya S.Yamaguchi H.Rara T.Iwamoto M. J. Med. Chem. 1994, 37: 1200 -
6b
Kawaguchi T,Akatsuka H,Iijima T,Tsuboi Y,Mitsui T, andMurakami J. inventors; WO 2003082847. ; Chem. Abstr. 2003, 139, 292142 - 7
Boschelli DH.Bramer JB.Khtana SS.Sorenson RJ.Connor DT.Ferin MA.Wright CD.Lesch ME.Imre K.Okonkwo GC.Schrier DJ.Conroy MC.Ferguson E.Woelle J.Saxena U. J. Med. Chem. 1995, 38: 4597 -
8a
Yang Z.Liu HB.Lee CM.Chang HM.Wong HNC. J. Org. Chem. 1992, 57: 7248 -
8b
Kuo Y.-H.Wu C.-H. J. Nat. Prod. 1996, 59: 625 - 9
Lu J,Ma T,Nagpal S,Shen Q,Warshawsky AM,Ochoada JM, andYee YK. inventors; WO 2005051938. ; Chem. Abstr. 2005, 143, 43763 - 10
Frangin G, andMalik M. inventors; WO 9840067. ; Chem. Abstr. 1998, 129: 239887 -
11a
Jinno S.Okita T.Inouye K. Bioorg. Med. Chem. Lett. 1999, 9: 1029 -
11b
Varvaresou A.Iakovou K.Filippatos E.Souli C.Calogeropoulou T.Ioannidou I.Kourounakis AP.Pannecouque C.Witvrouw M.Padalko E.Neyts J.De Clercq E.Tsotinis A. Arzneim.-Forsch. 2001, 51: 156 - 12
Johansson G,Brandt P, andNilsson BM. inventors; WO 2005058858. ; Chem. Abstr. 2005, 143, 97253 -
13a
Ohemeng KA.Appollina MA.Nguyen VN.Schwender CF.Singer M.Steber M.Ansell J.Argentieri D.Hageman W. J. Med. Chem. 1994, 37: 3663 -
13b
Ecker G.Chiba P.Hitzler M.Schmid D.Visser K.Cordes HP.Csoellei J.Seydel JK.Schaper K.-J. J. Med. Chem. 1996, 39: 4767 -
13c
Ashwood VA.Field MJ.Horwell DC.Julien-Larose C.Lewthwaite RA.McCleary S.Pritchard MC.Raphy J.Singh L. J. Med. Chem. 2001, 44: 2276 -
13d
Murthy VS.Kulkarni VM. Bioorg. Med. Chem. 2002, 10: 2267 -
13e
Collini MD.Kaufman DH.Manas ES.Harris HA.Henderson RA.Xu ZB.Unwalla RJ.Miller CP. Bioorg. Med. Chem. Lett. 2004, 14: 4925 -
14a
Arcadi A.Marinelli F.Cacchi S. Synthesis 1986, 749 -
14b
Arcadi A.Cacchi S.Del Rosario M.Fabrizi G.Marinelli F. J. Org. Chem. 1996, 61: 9280 - For a recent review on the palladium-catalyzed construction and functionalization of benzo[b]furans, see:
-
14c
Cacchi S.Fabrizi G.Goggiamani A. Curr. Org. Chem. 2006, 10: 1423 - For reviews on the chemistry of cardanol, see:
-
15a
Tyman JHP. Chem. Soc. Rev. 1979, 8: 499 -
15b
Attanasi OA.Buratti S.Filippone P. Chim. Ind. (Milan) 1996, 78: 693 - 16
Hu Y.Nawoschik KJ.Ma J.Fathi R.Yang Z. J. Org. Chem. 2004, 69: 2235 - 17
Arcadi A.Attanasi OA.Berretta S.Bianchi G.Filippone P. Synthesis 2006, 2523 - For some recent references, see:
-
18a
Genin E.Amengual R.Michelet V.Savignac M.Jutand A.Neuville L.Genet J.-P. Adv. Synth. Catal. 2004, 346: 1733 -
18b
Liang B.Dai M.Chen J.Yang Z. J. Org. Chem. 2005, 70: 391 -
18c
Liang B.Huang M.You Z.Xiong Z.Lu K.Fathi R.Chen J.Yang Z. J. Org. Chem. 2005, 70: 6097 -
18d
Ohshita J.Nada D.Tada Y.Kimura Y.Yoshida H.Kunai A.Kunugi Y. J. Organomet. Chem. 2005, 690: 3951 -
18e
Batchu VR.Subramanian V.Parasuraman K.Swamy NK.Kumar S.Pal M. Tetrahedron 2005, 61: 9869 -
18f
Anderson KW.Buchwald SL. Angew. Chem. Int. Ed. 2005, 44: 6173 -
18g
Gil-Molto J.Karlstroem S.Najera C. Tetrahedron 2005, 61: 12168 -
18h
Tremblay-Morin J.-P.Ali H.van Lier JE. Tetrahedron Lett. 2005, 46: 6999 -
18i
Xue C.Luo F.-T.Chen J.Liu H. Anal. Chim. Acta 2006, 569: 27 -
18j
Corma A.Garcia H.Primo A. J. Catal. 2006, 241: 123 -
18k
Li Y.Zhou P.Dai Z.Hu Z.Sun P.Bao J. New J. Chem. 2006, 30: 832 -
18l
Ali H.St-Jean O.Tremblay-Morin J.-P.van Lier JE. Tetrahedron Lett. 2006, 47: 8275 - 19
Songashira K.Tohda Y.Hagihara N. Tetrahedron Lett. 1975, 50: 4467