A Multicomponent Reaction between α-Substituted
Acroleins, Nitroalkanes and Paraformaldehyde: Efficient Construction
of Nitro δ-Lactol

Guoxi Xiong; Mohui Wei; Yirong Zhou; Yungui Li; Fanglin Zhang; Yuefa Gong

doi:10.1055/s-0030-1260194

PAPER

A Multicomponent Reaction between α-Substituted Acroleins, Nitroalkanes and Paraformaldehyde: Efficient Construction of Nitro δ-Lactol

Guoxi Xiong^a,b, Mohui Wei^a, Yirong Zhou^a, Yungui Li^a, Fanglin Zhang*^a, Yuefa Gong*^a
^a Department of Chemistry, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan 430074, P. R. of China
Fax: +86(27)87543632; e-Mail: hyvzfl@gmail.com; e-Mail: gongyf@mail.hust.edu.cn;
^b Research and Development Center, China Tobacco Hubei Industrial Co. Ltd., Wuhan 430040, P. R. of China

Abstract

Alle Artikel dieser Rubrik

Abstract

A base-catalyzed multicomponent cascade reaction between α-substituted acroleins, nitroalkanes, and paraformaldehyde that proceeded smoothly to give high yields of functionalized δ-lactols under mild conditions, is described. This methodology is useful in the development of a concise synthetic route to natural products (±)-manzacidin A and C.

Key words

multicomponent reaction - α-substituted acroleins - 1,8-diazabicyclo[5.4.0]undec-7-ene - δ-lactols

Volltext

Referenzen

References

1a González-López M. Shaw JT. Chem. Rev. 2009, 109: 164

1b Touré BB. Hall DG. Chem. Rev. 2009, 109: 4439

1c Grondal C. Jeanty M. Enders D. Nature Chem. 2010, 2: 167

2 Kobayashi J. Kanda F. Ishibashi M. Shigemori H. J. Org. Chem. 1991, 56: 4574

3a Berlinck RGS. Nat. Prod. Rep. 1999, 16: 339

3b Faulkner DJ. Nat. Prod. Rep. 2000, 17: 7

4a Namba K. Shinada T. Teramoto T. Ohfune Y. J. Am. Chem. Soc. 2000, 122: 10708

4b Wehn PM. Bois JD. J. Am. Chem. Soc. 2002, 124: 12950

4c Kano T. Hashimoto T. Maruoka K. J. Am. Chem. Soc. 2006, 128: 2174

4d Oe K. Shinada T. Ohfune Y. Tetrahedron Lett. 2008, 49: 7426

4e Wang Y. Liu X. Deng L. J. Am. Chem. Soc. 2006, 128: 3928

4f Sibi MP. Stanley LM. Soeta T. Org. Lett. 2007, 9: 1553

4g Tran K. Lombardi PJ. Leighton JL. Org. Lett. 2008, 10: 3165

5a Snider BB. Gu Y. Org. Lett. 2001, 3: 1761

5b Langlois N. Nguyen BKL. J. Org. Chem. 2004, 69: 7558

5c Isaacson J. Loo M. Kobayashi Y. Org. Lett. 2008, 10: 1461

6a Smith AB. Benowitz AB. Guzman MC. Sprengeler PA. Hirschmann R. Schweiger EJ. Bolin DR. Nagy Z. Campbell RM. Cox DC. Olson GL. J. Am. Chem. Soc. 1998, 120: 12704

6b Lee J. Han K.-C. Kang J.-H. Pearce LL. Lewin NE. Yan S. Benzaria S. Nicklaus MC. Blumberg PM. Marquez VE. J. Med. Chem. 2001, 44: 4309

6c Kang J.-H. Chung H.-E. Kim SY. Kim Y. Lee J. Lewin NE. Pearce LV. Blumberg PM. Marquezc VE. Bioorg. Med. Chem. 2003, 11: 2529

6d Huck BR. Gellman SH. J. Org. Chem. 2005, 70: 3353

6e Paliwal S. Reichard GA. Shah S. Wrobleski ML. Wang C. Stengone C. Tsui H.-C. Xiao D. Duffy RA. Lachowicz JE. Nomeir AA. Varty GB. Shih N.-Y. Bioorg. Med. Chem. Lett. 2008, 18: 4168

7 Zhang FL. Wei MH. Dong JF. Zhou YR. Lu DF. Gong YF. Yang XL. Adv. Synth. Catal. 2010, 352: 2875

8a Hojabri L. Hartikka A. Moghaddam FM. Arvidsson PI. Adv. Synth. Catal. 2007, 349: 740

8b Vakulya B. Varga S. Soós T. J. Org. Chem. 2008, 73: 3475

9 Erkkilä A. Pihko PM. J. Org. Chem. 2006, 71: 2538

Zusatzmaterial

Supporting Information