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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Crossref 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.