First Stereoselective Total
Synthesis of Naturally Occurring (6R)-6-(4-Oxopentyl)-5,6-dihydro-2H-pyran-2-one and Its (6S)-Enantiomer

Digambar Balaji Shinde; Boddu Shashi Kanth; Malampati Srilatha; Biswanath Das

doi:10.1055/s-0031-1289643

PAPER

First Stereoselective Total Synthesis of Naturally Occurring (6R)-6-(4-Oxopentyl)-5,6-dihydro-2H-pyran-2-one and Its (6S)-Enantiomer [¹]

Digambar Balaji Shinde, Boddu Shashi Kanth, Malampati Srilatha, Biswanath Das*
Organic Chemistry Division-1, Indian Institute of Chemical Technology, Hyderabad 500607, India
Fax: +91(40)27160512; e-Mail: biswanathdas@yahoo.com;

Abstract

All articles of this category

Abstract

(6R)-6-(4-Oxopentyl)-5,6-dihydro-2H-pyran-2-one, a naturally occurring α,β-unsaturated δ-lactone, and its (6S)-enantiomer have been synthesized stereoselectively starting from pentane-1,5-diol. The synthesis involves Maruoka asymmetric allylation and ring-closing metathesis as the key steps.

Key words

lactones - (6R)-6-(4-oxopent-2-enyl)-5,6-dihydro-2H-pyran-2-one - (6S)-6-(4-oxopent-2-enyl)-5,6-dihydro-2H-pyran-2-one - ring-closing metathesis - stereoselective synthesis

Full Text

References

1

Part 52 in the series, ‘Synthetic Studies on Natural Products’.

2a Hoffmann HMR. Rabe J. Angew. Chem., Int. Ed. Engl. 1985, 24: 94

2b Sam TW. Yeu CS. Jodynis-Liebert J. Murias M. Bloszyk E. Planta Med. 2000, 66: 199

2c Antonio MA. de Carvalho JE. Pillia RA. Bioorg. Med. Chem. 2005, 13: 2927

3 Marco JA. Carda M. Murga J. Falomir E. Tetrahedron 2007, 63: 2929

4 Maxwell A. Dabideen D. Reynolds WF. McLean S. J. Nat. Prod. 1998, 61: 815

5a Kretschmer M. Menche D. Synlett 2010, 2989

5b Yadav JS. Pandurangam T. Reddy VVB. Reddy BVS. Synthesis 2010, 4300

5c Ghosh AK. Dawson ZL. Synthesis 2009, 2992

5d Shibahara S. Fujino M. Tashiro Y. Okamoto N. Esumi T. Takahashi K. Ishihara J. Hatakeyama S. Synthesis 2009, 2935

6a Das B. Laxminarayana K. Krishnaiah M. Kumar DN. Bioorg. Med. Chem. Lett. 2009, 19: 6396

6b Das B. Suneel K. Satyalakshmi G. Tetrahedron: Asymmetry 2009, 20: 1536

6c Das B. Veeranjaneyulu B. Balasubramanyam P. Srilatha M. Tetrahedron: Asymmetry 2010, 21: 2762

6d Das B. Nagendra S. Reddy CR. Tetrahedron: Asymmetry 2011, 22: 1249

7a Hanawa H. Hashimoto T. Maruoka K. J. Am. Chem. Soc. 2003, 125: 1708

7b Das B. Shinde DB. Kanth BS. Kamle A. Kumar CG. Eur. J. Med. Chem. 2011, 46: 3124

8a Grubbs RH. Miller SJ. Fu GC. Acc. Chem. Res. 1995, 28: 446

8b Trnka TM. Grubbs RH. Acc. Chem. Res. 2001, 34: 18

8c Grubbs RH. Tetrahedron 2004, 60: 7117