First Total Synthesis of the Irciniasulfonic Acids

Adrian P. Dobbs; Alberto Venturelli; Laura A. Butler; Robert J. Parker

doi:10.1055/s-2005-862387

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 2005(4): 652-654
DOI: 10.1055/s-2005-862387

LETTER

First Total Synthesis of the Irciniasulfonic Acids

Adrian P. Dobbs*^a, Alberto Venturelli^a,b, Laura A. Butler^a, Robert J. Parker^a
^a Department of Chemistry, University of Exeter, Stocker Road, Exeter, EX4 4QD, UK
Fax: +44(1392)263434; e-Mail: A.Dobbs@exeter.ac.uk;
^b Dipartimento di Scienze Farmaceutiche, Università degli Studi di Modena e Reggio Emilia, Via G. Campi n. 183, 41110 Modena, Italy

Further Information

Publication History

Received 22 September 2004
Publication Date:
22 February 2005 (online)

Abstract
Full Text
References

Buy Article Permissions and Reprints All articles of this category

Abstract

A flexible and concise first total synthesis of the irciniasulfonic acids is reported.

Key words

total synthesis - irciniasulfonic acid - multidrug resistance modulator

References

1 Kawakami A. Miyamoto T. Higuchi R. Uchiumi T. Kuwano M. Van Soest RWM. Tetrahedron Lett. 2001, 42: 3335

Crossref Search in Google Scholar
2 Nagle DG. Zhou Y.-D. Mora FD. Mohammed KA. Kim Y.-P. Curr. Med. Chem. 2004, 11: 1725

Search in Google Scholar
3 Yamaguchi M. Nobayashi Y. Hirao I. Tetrahedron 1984, 40: 4261

Crossref Search in Google Scholar
4a Suzuki T. Saimoto H. Tomioka H. Oshima K. Nozaki H. Tetrahedron Lett. 1982, 23: 3597

Crossref Search in Google Scholar
4b Matthews RS. Eickhoff DJ. J. Org. Chem. 1985, 50: 3923

Crossref Search in Google Scholar
5a Schweitzer S. Voss G. Gerlach H. Liebigs Ann. Chem. 1994, 189

Crossref
5b Hamada T. Daikai K. Irie R. Katsuki T. Tetrahedron: Asymmetry 1995, 6: 2441

Crossref Search in Google Scholar
6 Vuligonda V. Thacher SM. Chandraratna RAS. J. Med. Chem. 2001, 44: 2298

Crossref Search in Google Scholar
7 Bachi MD. Bar-Ner N. Melman A. J. Org. Chem. 1996, 61: 7116

Crossref Search in Google Scholar
8a Dower WV. Peter K. Vollhardt C. Tetrahedron 1986, 42: 1873

Crossref Search in Google Scholar
8b Spiteller D. Boland W. J. Org. Chem. 2003, 68: 8743

Crossref Search in Google Scholar
9 Ley SV. Santafianos D. Blaney WM. Simmonds MSJ. Tetrahedron Lett. 1987, 28: 221

Crossref Search in Google Scholar
10 Raederstorff D. Shu AYL. Thompson JE. Djerassi C. J. Org. Chem. 1987, 52: 2337

Search in Google Scholar
11 A related approach to (5Z,9Z)-dienoic acids has been reported. See: Carballeira NM. Emiliano A. Guzmán A. Chem. Phys. Lipids 1999, 100: 33

Search in Google Scholar
12 Watanabe T. Hayashi K. Yoshimatsu S. Sakai K. Takeyama S. Takashima K. J. Med. Chem. 1980, 23: 50

Crossref Search in Google Scholar

13

All compounds gave satisfactory analytical and spectroscopic data. Compound data for the three natural products in good agreement with the values given in ref. 1.