Enantiomerically Pure Allylboronic Esters as Versatile Reagents in the Enantioselective Synthesis of Dihydro-α-pyrone-Containing Natural Products

Sean Bartlett; Dietrich Böse; Daniel Ghori; Bastian Mechsner; Jörg Pietruszka

doi:10.1055/s-0032-1318440

Synthesis, Table of Contents

Synthesis 2013; 45(8): 1106-1114
DOI: 10.1055/s-0032-1318440

paper

Enantiomerically Pure Allylboronic Esters as Versatile Reagents in the Enantioselective Synthesis of Dihydro-α-pyrone-Containing Natural Products

Sean Bartlett

^aSchool of Chemistry, University of Bristol, Cantock’s Close, Bristol BS8 1TS, UK

,

Dietrich Böse

^bInstitut für Bioorganische Chemie der Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich, Stetternicher Forst, Geb. 15.8, 52426 Jülich, Germany Fax: +49(2461)611669 Email: j.pietruszka@fz-juelich.de

,

Daniel Ghori

^bInstitut für Bioorganische Chemie der Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich, Stetternicher Forst, Geb. 15.8, 52426 Jülich, Germany Fax: +49(2461)611669 Email: j.pietruszka@fz-juelich.de

,

Bastian Mechsner

^bInstitut für Bioorganische Chemie der Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich, Stetternicher Forst, Geb. 15.8, 52426 Jülich, Germany Fax: +49(2461)611669 Email: j.pietruszka@fz-juelich.de

,

Jörg Pietruszka*

^bInstitut für Bioorganische Chemie der Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich, Stetternicher Forst, Geb. 15.8, 52426 Jülich, Germany Fax: +49(2461)611669 Email: j.pietruszka@fz-juelich.de

› Author Affiliations

Abstract

All articles of this category

Abstract

A short and efficient enantio- and diastereoselective synthesis of different representatives from the class of dihydro-α-pyrone natural products, including both enantiomers of goniothalamin, massoia lactone, parasorbic acid, and some derivatives is presented. It is based on the application of enantiopure α-chiral allylboronic esters in allyl additions.

Key words

natural products - goniothalamin - allyl addition - boronic ester - dihydro-α-pyrones

Full Text

References

References

1a Cavalheiro AJ, Yoshida M. Phytochemistry 2000; 53: 811
1b Hlubucek J, Robertson A. Aust. J. Chem. 1967; 20: 2199
1c Jewers K, Davis JB, Dougan J, Manchanda AH, Blunden G, Kyi A, Wetchapinan S. Phytochemistry 1972; 11: 2025
1d Juliawaty LD, Kitajima M, Takayama H, Achmad SA, Aimi N. Phytochemistry 2000; 54: 989

2a Fornari FA, Randolph JK, Yalowich JC, Ritke MK, Gewirtz DA. Mol. Pharmacol. 1994; 45: 649
2b Al-Qubaisi M, Rozita R, Yeap S.-K, Omar A.-R, Ali A.-M, Alitheen NB. Molecules 2011; 16: 2944
2c de Fátima Â, Marquissolo C, de Albuquerque S, Carraro-Abrahão AA, Pilli RA. Eur. J. Med. Chem. 2006; 41: 1210
2d Chen W.-Y, Wu C.-C, Lan Y.-H, Chang F.-R, Teng C.-M, Wu Y.-C. Eur. J. Pharmacol. 2005; 522: 20
2e Tan C, Tasaka H, Yu K.-P, Murphy ML, Karnofsky DA. Cancer 1967; 20: 333
2f de Fátima Â, Kohn LK, de Carvalho JE, Pilli RA. Bioorg. Med. Chem. 2006; 14: 622
2g Barcelos RC, Pastre JC, Caixeta V, Vendramini-Costa DB, de Carvalho JE, Pilli RA. Bioorg. Med. Chem. 2012; 20: 3635
2h Vendramini-Costa DB, de Castro IB. D, Ruiz AL. T. G, Marquissolo C, Pilli RA, de Carvalho JE. Bioorg. Med. Chem. 2010; 18: 6742

3 de Fátima Â, Kohn LK, Antônio MA, de Carvalho JE, Pilli RA. Bioorg. Med. Chem. 2005; 13: 2927

4a Ramachandran PV, Reddy MV. R, Brown HC. Tetrahedron Lett. 2000; 41: 583
4b Harsh P, O’Doherty GA. Tetrahedron 2009; 65: 5051
4c Ram Reddy MV, Brown HC, Ramachandran PV. J. Organomet. Chem. 2001; 624: 239

5 de Fátima Â, Pilli RA. Tetrahedron Lett. 2003; 44: 8721

6a Gruttadauria M, Lo Meo P, Noto R. Tetrahedron Lett. 2004; 45: 83
6b Sundby E, Perk L, Anthonsen T, Jørgen Aasen A, Vidar Hansen T. Tetrahedron 2004; 60: 521

7 Pospíšil J, Markó IE. Tetrahedron Lett. 2006; 47: 5933
8 Bose DS, Reddy AV. N, Srikanth B. Synthesis 2008; 2323

9a Fernández E, Pietruszka J. Synlett 2009; 1474
9b Fernández E, Pietruszka J, Frey W. J. Org. Chem. 2010; 75: 5580
9c Böse D, Fernández E, Pietruszka J. J. Org. Chem. 2011; 76: 3463

10 Zhou FS, Tang WD, Mu Q, Yang GX, Wang Y, Liang GL, Lou LG. Chem. Pharm. Bull. 2005; 53: 1387

11a Procter G, Russell AT, Murphy PJ, Tan TS, Mather AN. Tetrahedron 1988; 44: 3953
11b Shao L, Kawano H, Saburi M, Uchida Y. Tetrahedron 1993; 49: 1997

12 Oliveira JM. R, Freitas JC, Comasseto JV, Menezes PH. Tetrahedron 2011; 67: 3003

For alternative reports on the synthesis of goniothalamin and analogues, see for instance:

13a Virolleaud M.-A, Bressy C, Piva O. Tetrahedron Lett. 2003; 44: 8081
13b Dixon DJ, Ley SV, Tate EW. J. Chem. Soc., Perkin Trans. 1 1998; 3125
13c Bazán-Tejeda B, Bluet G, Broustal G, Campagne J.-M. Chem. Eur. J. 2006; 12: 8358
13d Quitschalle M, Christmann M, Bhatt U, Kalesse M. Tetrahedron Lett. 2001; 42: 1263
13e Sabitha G, Sudhakar K, Yadav JS. Tetrahedron Lett. 2006; 47: 8599
13f Job A, Wolberg M, Müller M, Enders D. Synlett 2001; 1796
13g Henkel B, Kunath A, Schick H. Liebigs Ann. Chem. 1992; 809
13h Bischop M, Pietruszka J. Synlett 2011; 2689
13i Fischer T, Pietruszka J. Adv. Synth. Catal. 2012; 354: 2521

Supplementary Material

Supporting Information