Concise Total Synthesis of
Vicenistatin

Hayato Fukuda; Shiina Nakamura; Tadashi Eguchi; Yoshiharu Iwabuchi; Naoki Kanoh

doi:10.1055/s-0030-1258574

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Synlett 2010(17): 2589-2592
DOI: 10.1055/s-0030-1258574

LETTER

Concise Total Synthesis of Vicenistatin

Hayato Fukuda^a, Shiina Nakamura^a, Tadashi Eguchi^b, Yoshiharu Iwabuchi^a, Naoki Kanoh*^a
^a Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan
Fax: +81(22)7956847; e-Mail: kanoh@mail.pharm.tohoku.ac.jp;
^b Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan

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Publication History

Received 21 July 2010
Publication Date:
23 September 2010 (online)

Abstract
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Abstract

A highly convergent total synthesis of macrocyclic lactam glycoside vicenistatin is described. Key features of the synthesis include rapid assembly of the macrolactam part and macrocyclic ring closure via intramolecular Stille coupling.

Key words

vicenistatin - macrolactam - vicenisamine - total synthesis

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References and Notes

1 Shindo K. Kamishohara M. Odagawa A. Matsuoka M. Kawai H. J. Antibiot. 1993, 46: 1076

Search in Google Scholar
2 Arai H. Matsushima Y. Eguchi T. Shindo K. Kakinuma K. Tetrahedron Lett. 1998, 39: 3181

Crossref Search in Google Scholar
3a Matsushima Y. Itoh H. Eguchi T. Kakinuma K.
J. Antibiot. 1998, 51: 688

Search in Google Scholar
3b Matsushima Y. Itoh H. Nakayama T. Horiuchi S. Eguchi T. Kakinuma K. J. Chem. Soc., Perkin Trans. 1 2002, 949
4 Matsushima Y. Nakayama T. Fujita M. Bhandari R. Eguchi T. Shindo K. Kakinuma K. J. Antibiot. 2001, 54: 211

Search in Google Scholar
5 Gassner NC. Tamble CM. Bock JE. Cotton N. White KN. Tenney K. St. Onge RP. Proctor MJ. Giaever G. Nislow C. Davis RW. Crews P. Holman TR. Lokey RS. J. Nat. Prod. 2007, 70: 383

Crossref Search in Google Scholar
6 Roush WR. Brown RJ. J. Org. Chem. 1983, 48: 5093

Crossref Search in Google Scholar
7 Martin SF. Dodge JA. Tetrahedron Lett. 1991, 32: 3017

Crossref Search in Google Scholar
8 Roush WR. James RA. Aust. J. Chem. 2002, 55: 141

Crossref Search in Google Scholar
9a Nicolaou KC. Seitz SP. Papahatjis DP. J. Am. Chem. Soc. 1983, 105: 2430

Search in Google Scholar
9b Nicolaou KC. Dolle RE. Papahatjis DP. Randall JL. J. Am. Chem. Soc. 1984, 106: 4189

Search in Google Scholar
10 Wipf P. Lim S. Angew. Chem., Int. Ed. Engl. 1993, 32: 1068

Crossref Search in Google Scholar
11 Dess DB. Martin JC. J. Org. Chem. 1983, 48: 4155

Crossref Search in Google Scholar
12 Brown HC. Bhat KS. Randad RS. J. Org. Chem. 1989, 54: 1570

Search in Google Scholar
13 Garber SB. Kingsbury JS. Gray BL. Hoveyda AH. J. Am. Chem. Soc. 2000, 122: 8168

Search in Google Scholar
14 Paquette LA. Duan MS. Konetzki I. Kempmann C.
J. Am. Chem. Soc. 2002, 124: 4257

Crossref PubMed Search in Google Scholar
15 Darwish A. Lang A. Kim T. Chong JM. Org. Lett. 2008, 10: 861

Crossref Search in Google Scholar
16 Schmidt JP. Beltran-Rodil S. Cox RJ. McAllister GD. Reid M. Taylor RJK. Org. Lett. 2007, 9: 4041

Crossref PubMed Search in Google Scholar
17 Nicolaou KC. Murphy F. Barluenga S. Ohshima T. Wei H. Xu J. Gray DLF. Baudoin O. J. Am. Chem. Soc. 2000, 122: 3830

Crossref Search in Google Scholar
18 Hashimoto S. Hayashi M. Noyori R. Tetrahedron Lett. 1984, 25: 1379

Crossref Search in Google Scholar
19 Mukaiyama T. Takashima T. Katsurada M. Aizawa H. Chem. Lett. 1991, 533

Crossref

Supplementary Material

Supporting Information