Application of Iminophosphorane-Based Methodologies for the Synthesis of Natural Products

Pilar M. Fresneda; Pedro Molina

doi:10.1055/s-2003-43338

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synlett 2004(1): 1-17
DOI: 10.1055/s-2003-43338

ACCOUNT

Application of Iminophosphorane-Based Methodologies for the Synthesis of Natural Products

Pilar M. Fresneda*, Pedro Molina
Departamento de Química Orgánica, Facultad de Química, Universidad de Murcia, Campus de Espinardo, 30071, Murcia, Spain
Fax: +34(968)364149; e-Mail: pmolina@um.es; e-Mail: fresneda@um.es;

Further Information

Publication History

Received 15 July 2003
Publication Date:
26 November 2003 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

Four methodologies based on the aza-Wittig reaction have been used for the preparation of the wide variety of nitrogen-containing natural products. The synthesis of quinoline, β-carboline, pyrimidine, oxazole and imidazole alkaloids, by using these methodologies are presented.

1 Introduction

2 Intramolecular aza-Wittig Reaction

3 Tandem aza-Wittig/Electrocyclic Ring-Closure

4 Tandem aza-Wittig/Heterocumulene-Mediated Annelation

5 Tandem aza-Wittig/Intramolecular Halide Displacement

Key words

iminophosphoranes - heterocumulenes - aza-Wittig reaction - tandem process - alkaloids

References

Reviews:
1a Barluenga J. Palacios F. Org. Prep. Proced. Int. 1991, 1

Google Scholar
1b Gusar NI. Russ. Chem. Rev. 1991, 60: 146

Google Scholar
1c Gololobov YG. Kasukhin L. Tetrahedron 1992, 48: 1353

Google Scholar
1d Eguchi S. Matsushita K. Yamashita K. Org. Prep. Proced. Int. 1992, 209

Google Scholar
1e Molina P. Vilaplana MJ. Synthesis 1994, 1197

Google Scholar
1f Wammhoff H. Richardt G. Stölben S. Adv. Heterocycl. Chem. 1999, 64: 159

Google Scholar
1g Eguchi S. Okano T. Okawa T. Rec. Res. Devel. Org. Chem. 1997, 1: 337

Google Scholar
2 Williams DR. Brown DL. Benbow JW. J. Am. Chem. Soc. 1989, 11: 1923

Google Scholar
3 Eguchi S. Yamashita K. Matsushita Y. Kakehi A. J. Org. Chem. 1995, 60: 4006

Crossref Google Scholar
4 Molina P. Díaz I. Tárraga A. Tetrahedron 1995, 19: 5617

Google Scholar
5 De Kimpe N. Stevens C. Tetrahedron 1995, 51: 2387

Crossref Google Scholar
6 Jiang B. Yang C.-G. Wang J. J. Org. Chem. 2001, 66: 4865

Crossref PubMed Google Scholar
7 Sha C.-K. Chiu R.-T. Yang C.-F. Yao N.-T. Tseng W.-H. Liao F.-L. Wang S.-L. J. Am. Chem. Soc. 1997, 119: 4130

Crossref Google Scholar
8 Dolle RE. Kruse LI. J. Chem. Soc., Chem. Commun. 1988, 133

Crossref Google Scholar
9 White JD. Cammack JH. Sakuma K. Rewcastle GW. Widener RK. J. Org. Chem. 1995, 60: 3600

Google Scholar
10 Takeuchi H. Eguchi S. Tetrahedron Lett. 1989, 3313

Crossref Google Scholar
11 Takeuchi H. Hagiwara S. Eguchi S. Tetrahedron 1989, 45: 6375

Crossref Google Scholar
12 Eguchi S. Takeuchi H. Matsushita Y. Heterocycles 1992, 33: 153

Google Scholar
13 Eguchi S. Suzuki T. Okawa T. Matsushita Y. Yashima E. Okamoto Y. J. Org. Chem. 1996, 61: 7316

Google Scholar
14 Snider BP. Busuyek MV. Tetrahedron 2001, 57: 3301

Crossref Google Scholar
15 He FM. Foxman BM. Snider BB. J. Am. Chem. Soc. 1998, 120: 6417

Crossref Google Scholar
16 He F. Snider BB. Synlett 1997, 483

Article in Thieme Connect Google Scholar
17 Marsden SP. Depew KM. Danishefsky SJ. J. Am. Chem. Soc. 1994, 116: 11143

Crossref Google Scholar
18 Kennedy M. Moody CJ. Rees CW. Vaquero JJ. J. Chem. Soc., Perkin Trans. 1 1987, 1395

Crossref Google Scholar
19 Sugimori T. Okawa T. Eguchi S. Kakehi A. Yashima E. Okamoto Y. Chem. Lett. 1997, 869

Crossref Google Scholar
20 Sugimori T. Okawa T. Eguchi S. Kakehi A. Yashima E. Okamoto Y. Tetrahedron 1998, 54: 7997

Crossref Google Scholar
21 Okawa T. Sugimori T. Eguchi S. Kakehi A. Heterocycles 1998, 47: 375

Google Scholar
22 Molina P. García-Zafra S. Fresneda PM. Synlett 1995, 43

Article in Thieme Connect Google Scholar
23 Molina P. Vidal A. Barquero A. Synthesis 1996, 1119

Google Scholar
24 Molina P. Vidal A. Tovar F. Synthesis 1997, 963

Article in Thieme Connect Google Scholar
25 Molina P. Murcia F. Fresneda PM. Tetrahedron Lett. 1994, 35: 1453

Crossref Google Scholar
26 Molina P. Fresneda PM. Cánovas M. Tetrahedron Lett. 1992, 33: 2891

Google Scholar
27 Molina P. Fresneda PM. García-Zafra S. Tetrahedron Lett. 1995, 36: 3581

Google Scholar
28 Molina P. Fresneda PM. García-Zafra S. Almendros P. Tetrahedron Lett. 1994, 35: 8851

Crossref Google Scholar
29 Molina P. Fresneda PM. García-Zafra S. Tetrahedron Lett. 1996, 37, 9353

Google Scholar
30a Molina P. Alajarín M. Vidal A. J. Chem. Soc., Chem. Commun. 1990, 1277

Google Scholar
30b Molina P. Alajarín M. Vidal A. Sanchez-Andrada P. J. Org. Chem. 1992, 57: 929

Google Scholar
31 Molina P. Fresneda PM. Delgado S. Synthesis 1999, 326

Article in Thieme Connect Google Scholar
32a Fresneda PM. Molina P. Delgado S. Tetrahedron Lett. 1999, 40: 7275

Crossref Google Scholar
32b Fresneda PM. Molina P. Delgado S. Tetrahedron 2001, 57: 6197

Crossref Google Scholar
33 Molina P. Fresneda PM. Sanz MA. J. Org. Chem. 1999, 64: 2540

Crossref Google Scholar
34a Evans DA. Britton TC. Dorow RL. Dellaria JF. Tetrahedron 1988, 44: 5525

Google Scholar
34b Evans DA. Ellman JA. Dorow RL. J. Am. Chem. Soc. 1990, 112: 4011

Google Scholar
34c Evans DA. Devries KM. Tetrahedron Lett. 1992, 1189

Google Scholar
34d Pearson AJ. Zhang P. Lee K. J. Org. Chem. 1996, 61: 6581

Google Scholar
35 Fresneda PM. Molina P. Sanz MA. Tetrahedron Lett. 2001, 42: 851

Crossref Google Scholar
36 Molina P. Almendros P. Fresneda PM. Tetrahedron Lett. 1994, 35: 2235

Crossref Google Scholar
37a Molina P. Fresneda PM. Almendros P. Tetrahedron Lett. 1992, 33: 4491

Google Scholar
37b Molina P. Almendros P. Fresneda PM. Tetrahedron 1994, 50: 2241

Google Scholar
38a Fresneda PM. Molina P. Delgado S. Bleda JA. Tetrahedron Lett. 2000, 41: 4777

Crossref Google Scholar
38b Molina P. Fresneda PM. Delgado S. Bleda JA. Tetrahedron Lett. 2002, 43: 1005

Crossref Google Scholar
38c Molina P. Fresneda PM. Delgado S. J. Org. Chem. 2003, 68: 489

Crossref Google Scholar
39 Bredereck M. Effenberger F. Botsch H. Rehn H. Chem. Ber. 1965, 98: 1081

Crossref Google Scholar
40 Zbiral E. Bauer E. Stroh J. Monatsh. Chem. 1971, 102: 168

Crossref Google Scholar
41 Molina P. Fresneda PM. Almendros P. Synthesis 1993, 55

Google Scholar
42 Molina P. Fresneda PM. Almendros P. Heterocycles 1993, 36: 2255

Crossref Google Scholar
43 Fresneda PM. Molina P. Sanz MA. Synlett 2001, 218

Google Scholar
44 Fresneda PM. Molina P. Sanz MA. Synlett 2000, 1190

Article in Thieme Connect Google Scholar