The Oxa-Pictet-Spengler Reaction of 1-(3-Furyl)alkan-2-ols

William H.  Miles; Susan K.  Heinsohn; Megan K.  Brennan; Daniel T.  Swarr; Patrick M.  Eidam; Kathy A.  Gelato

doi:10.1055/s-2002-33336

PAPER

The Oxa-Pictet-Spengler Reaction of 1-(3-Furyl)alkan-2-ols

William H. Miles*, Susan K. Heinsohn, Megan K. Brennan, Daniel T. Swarr, Patrick M. Eidam, Kathy A. Gelato
Department of Chemistry, Lafayette College, Easton, PA 18042, USA
Fax: +1(610)3305714; e-Mail: milesw@lafayette.edu;

Abstract

All articles of this category

Abstract

The oxa-Pictet-Spengler reaction of 1-(3-furyl)alkan-2-ols with aldehydes catalyzed by p-toluenesulfonic acid gives good yields of the corresponding cis-5,7-disubstituted 4,5-dihydro-7H-furano[2,3-c]pyrans.

Key words

oxa-Pictet-Spengler reaction - furans - cyclizations - Lewis acids - ene reactions

Full Text

References

1 Cox ED. Cook JM. Chem. Rev. 1995, 95: 1797

2a Wünsch B. Zott M. Liebigs Ann. Chem. 1992, 39

2b Gatta F. Settimj G. J. Heterocycl. Chem. 1983, 20: 1267

2c Kametani T. Kigasawa K. Hiiragi M. Ishimaru H. Wagatsuma N. Haga S. Kusama O. J. Heterocycl. Chem. 1975, 12: 851

2d Guiso M. Marra C. Cavarischia C. Tetrahedron Lett. 2001, 42: 6531

3a Satoh D. Hashimoto T. Aoyama K. Yakugaku Zasshi 1974, 94: 774 ; Chem. Abstr. 1974, 81, 105333

3b Satoh D. Hashimoto T. Aoyama K. Yakugaku Zasshi 1975, 95: 1183 ; Chem. Abstr. 1976, 84, 17073

3c Satoh D, and Aoyama K. inventors; Ger. Offen. 2051496. ; Chem. Abstr. 1971, 75, 49451

4a DeNinno MP. Schoenleber R. Asin KE. MacKenzie R. Kebabian JW. J. Med. Chem. 1990, 33: 2948

4b DeNinno MP. Perner RJ. Morton HE. DiDomenico S. J. Org. Chem. 1992, 57: 7115

4c TenBrink RE. Bergh CL. Duncan JN. Harris DW. Huff RM. Lahti RA. Lawson CF. Lutzke BS. Martin IJ. Rees SA. Schlachter SK. Sih JC. Smith MW. J. Med. Chem. 1996, 39: 2435

4d Ennis MD. Ghazal NB. Hoffman RL. Smith MW. Schlachter SK. Lawson CF. Im WB. Pregenzer JF. Svensson KA. Lewis RA. Hall ED. Sutter DM. Harris LT. McCall RB. J. Med. Chem. 1998, 41: 2180

4e Unterhalt B. Heppert U. Pharmazie 2001, 56: 445

4f Rama NH. Saeed A. J. Chem. Soc. Pak. 1992, 14: 286 ; Chem. Abstr. 1993, 119, 225782

4g Xu Y. Kohlman DT. Liang SX. Erikkson C. Org. Lett. 1999, 1: 1599

5a Wünsch B. Zott M. Tetrahedron: Asymmetry 1993, 4: 2307

5b Giles RGF. Rickards RW. Senanayake BS. J. Chem. Soc., Perkin Trans. 1 1996, 2241

5c Steyn PS. Holzapfel CW. Tetrahedron 1967, 23: 4449

5d Mohler DL. Thompson DW. Tetrahedron Lett. 1987, 28: 2567

5e Cutler HG. Majetich G. Tian X. Spearing P. J. Agric. Food Chem. 1997, 45: 1422

5f Kaufman TS. Bernardi CR. Cipulli M. Silveira CC. Molecules 2000, 5: 493

6 For a review of isochroman chemistry, see: Markaryan EA. Samodurova AG. Russ. Chem. Rev. 1989, 58: 479

7a Miles WH. Berreth CL. Smiley PM. Tetrahedron Lett. 1993, 34: 5221

7b Miles WH. Berreth CL. Anderton CA. Tetrahedron Lett. 1996, 37: 7893

7c Miles WH. Fialcowitz EJ. Halstead ES. Tetrahedron 2001, 57: 9925

8 Bhatt U. Christmann M. Quitschalle M. Claus E. Kalesse M. J. Org. Chem. 2001, 66: 1885

9 Jaber JJ. Mitsui K. Rychnovsky SD. J. Org. Chem. 2001, 66: 4679 ; and references cited therein

10 Tanis SP. Deaton MV. Dixon LA. McMills MC. Raggon JW. Collins MA. J. Org. Chem. 1998, 63: 6914 ; and references cited therein

11 Lipshutz BH. Chem. Rev. 1986, 86: 795