Diastereo- and Enantioselective Synthesis of Polyfunctionalized Diquinanes, Hydrindanes, and Decalins Bearing a Hydroxyl Group at the Ring Junction

Clément F. Heinrich; Clovis Peter; Laurence Miesch; Philippe Geoffroy; Michel Miesch

doi:10.1055/s-0035-1561858

Synthesis, Table of Contents

Synthesis 2016; 48(11): 1607-1615
DOI: 10.1055/s-0035-1561858

short review

Diastereo- and Enantioselective Synthesis of Polyfunctionalized Diquinanes, Hydrindanes, and Decalins Bearing a Hydroxyl Group at the Ring Junction

Authors

Clément F. Heinrich

Université de Strasbourg, Institut de Chimie – UMR 7177, 1 rue Blaise Pascal, BP296/R8, 67008 Strasbourg-Cedex, France Email: m.miesch@unistra.fr
Clovis Peter

Université de Strasbourg, Institut de Chimie – UMR 7177, 1 rue Blaise Pascal, BP296/R8, 67008 Strasbourg-Cedex, France Email: m.miesch@unistra.fr
Laurence Miesch

Université de Strasbourg, Institut de Chimie – UMR 7177, 1 rue Blaise Pascal, BP296/R8, 67008 Strasbourg-Cedex, France Email: m.miesch@unistra.fr
Philippe Geoffroy

Université de Strasbourg, Institut de Chimie – UMR 7177, 1 rue Blaise Pascal, BP296/R8, 67008 Strasbourg-Cedex, France Email: m.miesch@unistra.fr
Michel Miesch*

Université de Strasbourg, Institut de Chimie – UMR 7177, 1 rue Blaise Pascal, BP296/R8, 67008 Strasbourg-Cedex, France Email: m.miesch@unistra.fr

Abstract

All articles of this category

Abstract

Bicyclo[3.3.0]octan-1-ol (diquinane ring system), bicyclo[4.3.0]nonan-1-ol (hydrindane ring system), and bicyclo[4.4.0]decan-1-ol (decalin ring system) belong to the medium-sized rings family which represent important scaffolds of numerous natural products. Thus, the development of new routes leading to such scaffolds is of importance because such carbocycles are ubiquitous in numerous biologically active compounds. This short review will focus on the main approaches reported since 2000, leading to these bicyclic scaffolds with high diastereo- and/or enantioselectivities.

1 Introduction

2 Diastereoselective Approaches

3 Diastereo- and Enantioselective Catalytic Approaches

4 Conclusion

Key words

bicyclo[n.m.0]alkan-1-ol - cyclization - diastereoselectivity - enantioselectivity - metal catalysis

Full Text

References

References

1a Rukachaisirikul V, Tansakul C, Saithong S, Pakawatchai C, Isaka M, Suvannakad R. J. Nat. Prod. 2005; 68: 1674
1b Chang C.-H, Wen Z.-H, Wang S.-K, Duh C.-Y. J. Nat. Prod. 2008; 71: 619

2a Heasley B. Chem. Eur. J. 2012; 18: 3092
2b Shukla YJ, Khan IA, Geoffroy P, Miesch M. Stud. Nat. Prod. Chem. 2013; 40: 327

3 Pranithanchai W, Karalai C, Ponglimanont C, Subhadhirasakul S, Chantrapromma K. Phytochemistry 2009; 70: 300
4 Zhang J, Li Y, Zhu R, Li L, Wang Y, Zhou J, Qiao Y, Zhang Z, Lou H. J. Nat. Prod. 2015; 78: 208

5a Molander GA, Le Huérou Y, Brown GA. J. Org. Chem. 2001; 66: 4511
5b Molander GA, Czako B, Rheam M. J. Org. Chem. 2007; 72: 1755

6 Kakiuchi K, Fujioka Y, Yamamura H, Tsutsumi K, Morimoto T, Kurosawa H. Tetrahedron Lett. 2001; 42: 7595

7a Wender PA, Gamber GG, Hubbard RD, Zhang L. J. Am. Chem. Soc. 2002; 124: 2876
7b Jiao L, Yuan C, Yu Z.-X. J. Am. Chem. Soc. 2008; 130: 4421

8a Huddleston RR, Krische MJ. Org. Lett. 2003; 5: 1143
8b Koech PK, Krische MJ. Org. Lett. 2004; 6: 691

9 Chiu P, Szeto CP, Geng Z, Cheng KF. Org. Lett. 2001; 3: 1901
10 Chiu P, Szeto CP, Geng Z, Cheng KF. Tetrahedron Lett. 2001; 42: 4091
11 Chiu P, Leung SK. Chem. Commun. 2004; 2308
12 Chung WK, Chiu P. Synlett 2005; 55
13 Ressault B, Jaunet A, Geoffroy P, Goudedranche S, Miesch M. Org. Lett. 2012; 14: 366
14 Saito N, Sugimura Y, Sato Y. Org. Lett. 2010; 12: 3494
15 Beauseigneur A, Ericsson C, Renaud P, Schenk K. Org. Lett. 2009; 11: 3778

16a Wendling F, Miesch M. Org. Lett. 2001; 3: 2689
16b Klein A, Miesch M. Tetrahedron Lett. 2003; 44: 4483
16c Miesch M. Synthesis 2004; 746
16d Mota AJ, Klein A, Wendling F, Dedieu A, Miesch M. Eur. J. Org. Chem. 2005; 4346
16e Geoffroy P, Ballet M.-P, Finck S, Marchioni E, Miesch M. Tetrahedron 2010; 66: 7012

17 Klein A, Miesch M. Synthesis 2006; 2613
18 Heinrich CF, Miesch M, Miesch L. Org. Biomol. Chem. 2015; 13: 2153
19 Wang Y, Jaunet A, Geoffroy P, Miesch M. Org. Lett. 2013; 15: 6198

20a Miesch L, Rietsch V, Welsch T, Miesch M. Tetrahedron Lett. 2008; 49: 5053
20b Miesch L, Welsch T, Rietsch V, Miesch M. Chem. Eur. J. 2009; 15: 4394
20c Miesch M, Welsch T, Rietsch V, Miesch L. Strategies Tactics Org. Synth. 2013; 9: 203

21 Bocknack BM, Wang L.-C, Krische MJ. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 5421

22a Deschamp J, Riant O. Org. Lett. 2009; 11: 1217
22b Deschamp J, Hermant T, Riant O. Tetrahedron 2012; 68: 3457

23 Li N, Ou J, Miesch M, Chiu P. Org. Biomol. Chem. 2011; 9: 6143

24a Ou J, Wong W.-T, Chiu P. Tetrahedron 2012; 68: 3450
24b Ou J, Wong W.-T, Chiu P. Org. Biomol. Chem. 2012; 10: 5971

25 Burns AR, Gonzalez JS, Lam HW. Angew. Chem. Int. Ed. 2012; 51: 10827

26a Eder U, Sauer G, Wiechert R. Angew. Chem., Int. Ed. Engl. 1971; 10: 496
26b Hajos ZG, Parrish DR. J. Org. Chem. 1974; 39: 1615

27 Davies SG, Russell AJ, Sheppard RL, Smith AD, Thomson JE. Org. Biomol. Chem. 2007; 5: 3190 ; and references cited therein
28 Bradshaw B, Bonjoch J. Synlett 2012; 23: 337

29a Chandler CL, List B. J. Am. Chem. Soc. 2008; 130: 6737
29b See also: Diaz J, Goodman JM. Tetrahedron 2010; 66: 8021

30a Ema T, Oue Y, Akihara K, Miyazaki Y, Sakai T. Org. Lett. 2009; 11: 4866
30b Ema T, Akihara K, Obayashi R, Sakai T. Adv. Synth. Catal. 2012; 354: 3283
30c See also: Lathrop SP, Rovis T. J. Am. Chem. Soc. 2009; 131: 13628