Synthesis 2015; 47(08): 1117-1122
DOI: 10.1055/s-0034-1380177
paper
© Georg Thieme Verlag Stuttgart · New York

Tandem Prins and Friedel–Crafts Cyclizations for the Stereo­selective Synthesis of trans-Fused Hexahydro-1H-benzo[g]isochromene Derivatives

B. V. Subba Reddy*
a   Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India, Email: basireddy@iict.res.in
,
Ch. Syama Sundar
a   Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India, Email: basireddy@iict.res.in
b   Department of Chemistry, Sri Venkateswara University, Tirupati 517 502, India
,
M. Ramana Reddy
b   Department of Chemistry, Sri Venkateswara University, Tirupati 517 502, India
,
C. Suresh Reddy
b   Department of Chemistry, Sri Venkateswara University, Tirupati 517 502, India
,
B. Sridhar
c   Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India
› Author Affiliations
B. V. Subba Reddy*
a   Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India, Email: basireddy@iict.res.in
,
Ch. Syama Sundar
a   Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India, Email: basireddy@iict.res.in
b   Department of Chemistry, Sri Venkateswara University, Tirupati 517 502, India
,
M. Ramana Reddy
b   Department of Chemistry, Sri Venkateswara University, Tirupati 517 502, India
,
C. Suresh Reddy
b   Department of Chemistry, Sri Venkateswara University, Tirupati 517 502, India
,
B. Sridhar
c   Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India
› Author Affiliations
Further Information

Publication History

Received: 26 September 2014

Accepted after revision: 20 January 2015

Publication Date:
27 February 2015 (online)


Abstract

Aldehydes and ketones undergo smooth coupling with (4E)-3-benzyl-5-phenylpent-4-en-1-ol in the presence of scandium(III) triflate (10 mol%) and 4-toluenesulfonic acid (30 mol%) to give the corresponding trans-fused hexahydro-1H-benzo[g]isochromenes in good yields with excellent selectivity. This is the first example of the synthesis of a trans-fused hexahydro-1H-benzo[g]isochromene derivatives from an aldehyde and (4E)-3-benzyl-5-phenylpent-4-en-1-ol through tandem Prins and Friedel–Crafts cyclizations.

Supporting Information

 
  • References and Notes


    • For reviews on the Prins cyclization, see:
    • 1a Olier C, Kaafarani M, Gastaldi SS, Bertrand MP. Tetrahedron 2010; 66: 413
    • 1b Crane EA, Scheidt KA. Angew. Chem. Int. Ed. 2010; 49: 8316
    • 1c Adams DR, Bhatnagar SR. Synthesis 1977; 661
    • 2a Snider BB In Comprehensive Organic Synthesis . Vol. 2. Trost BM, Fleming I. Pergamon; Oxford: 1991. Chap. 2.1, 527
    • 2b Clarke PA, Santos S. Eur. J. Org. Chem. 2006; 2045
    • 2c Overman LE, Pennington LD. J. Org. Chem. 2003; 68: 7143
    • 2d Chio FK, Warne J, Gough D, Penny M, Green S, Coles SJ, Hursthouse MB, Jones P, Hassall L, McGuire TM, Dobbs AP. Tetrahedron 2011; 67: 5107
    • 2e Yang X.-F, Wang M, Zhang Y, Li C.-J. Synlett 2005; 1912
    • 3a Reddy BV. S, Borkar P, Yadav JS, Sridhar B, Grée R. J. Org. Chem. 2011; 76: 7677
    • 3b Reddy BV. S, Borkar P, Yadav JS, Reddy PP, Kunwar AC, Sridhar B, Grée R. Org. Biomol. Chem. 2012; 10: 1349
    • 3c Reddy BV. S, Kumar H, Borkar P, Yadav JS, Sridhar B. Eur. J. Org. Chem. 2013; 1993
    • 4a Suginome M, Ohmori Y, Ito Y. Chem. Commun. 2001; 1090
    • 4b Elsworth JD, Willis CL. Chem. Commun. 2008; 1587
    • 4c Spivey AC, Laraia L, Bayly AR, Rzepa HS, White AJ. P. Org. Lett. 2010; 12: 900
    • 4d Chen Z.-H, Tu Y.-Q, Zhang S.-Y, Zhang F.-M. Org. Lett. 2011; 13: 724
  • 5 Snider BB, Jackson AC. J. Org. Chem. 1983; 48: 1471
    • 6a Fernandes RA, Ingle AB, Chavan VP. Org. Biomol. Chem. 2012; 10: 4462
    • 6b Pillay A, Rousseau AL, Fernandes MA, de Koning CB. Org. Biomol. Chem. 2012; 10: 7809
    • 7a Ayres DC, Loike JD. Lignans: Chemical, Biological and Clinical Properties . Cambridge University Press; Cambridge: 1990
    • 7b Davies HM. L, Jin Q. Tetrahedron: Asymmetry 2003; 14: 941
    • 8a Kelly MG, Hartwell JL. J. Natl. Cancer Inst. 1954; 14: 967
    • 8b Imbert T. Biochimie 1998; 80: 207
  • 9 Bohlin L, Rosen B. Drug Discovery Today 1996; 1: 343
  • 10 Gordaliza M, Castro MA, Miguel del Corral JM, San Feliciano A. Curr. Pharm. Des. 2000; 6: 1811
    • 11a Gupta S, Das L, Datta AB, Poddar A, Janik ME, Bhattacharyya B. Biochemistry 2006; 45: 6467
    • 11b Damayanthi Y, Lown JW. Curr. Med. Chem. 1998; 5: 205
    • 11c Castro MA, Miguel del Corral JM, García PA, Rojo MV, De la Iglesia-Vicente J, Mollinedo F, Cuevas C, San Feliciano A. J. Med. Chem. 2010; 53: 983
    • 12a Reddy BV. S, Jalal S, Borkar P, Yadav JS, Reddy PP, Kunwar AC, Sridhar B. Org. Biomol. Chem. 2012; 10: 6562
    • 12b Reddy BV. S, Venkateswarlu A, Borkar P, Yadav JS, Kanakaraju M, Kunwar AC, Sridhar B. J. Org. Chem. 2013; 78: 6303
    • 12c Reddy BV. S, Medaboina D, Sridhar B, Singarapu KK. J. Org. Chem. 2013; 78: 8161
    • 12d Reddy BV. S, Reddy PS, Yadav JS, Sridhar B. Tetrahedron Lett. 2013; 54: 1392
    • 12e Reddy BV. S, Anjum SR, Reddy GM, Sridhar B. Tetrahedron Lett. 2014; 55: 5011
  • 13 Bunt AJ, Bailey CD, Cons BD, Edwards SJ, Elsworth JD, Pheko T, Willis CL. Angew. Chem. Int. Ed. 2012; 51: 3901
    • 14a Borkar P, van de Weghe P, Reddy BV. S, Yadav JS, Grée R. Chem. Commun. 2012; 48: 9316
    • 14b Breugst M, Grée R, Houk KN. J. Org. Chem. 2013; 78: 9892
    • 14c Reddy BV. S, Borkar P, Yadav JS, Sridhar B, Grée R. J. Org. Chem. 2011; 76: 7677
  • 15 Crystallographic data for compound 8a have been deposited with the accession number CCDC 994906, and can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk; Web site: www.ccdc.cam.ac.uk/conts/retrieving.html.