Total Synthesis of Prelaureatin

Kenshu  Fujiwaraa; Shin-ichiro  Souma; Hirofumi  Mishima; Akio  Murai

doi:10.1055/s-2002-33511

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 2002(9): 1493-1495
DOI: 10.1055/s-2002-33511

LETTER

Total Synthesis of Prelaureatin

Kenshu Fujiwaraa*^a, Shin-ichiro Souma^a, Hirofumi Mishima^a, Akio Murai*^a,b
^a Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan
Fax: +81(11)7062714; e-Mail: fjwkn@sci.hokudai.ac.jp;
^b Present address: 6-14-44 Asabu-cho, Kita-ku, Sapporo 001-0045, Japan
Fax: +81(11)7476963; e-Mail: amurai@rmail.plala.or.jp;

Further Information

Publication History

Received 14 May 2002
Publication Date:
17 September 2002 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

Total synthesis of prelaureatin, which is an 8-membered cyclic ether isolated from red alga Laurencia nipponica, has been achieved through a process including stereoselective introduction of two allyl groups starting from galactose pentaacetate, cleavage of the hexose ring, and transformation of an acyclic triene into an oxocene by selective ring-closing metathesis.

Key words

total synthesis - stereoselective synthesis - natural products - ethers - metathesis

References

1 Fukuzawa A. Takasugi Y. Murai A. Tetrahedron Lett. 1991, 32: 5597

Crossref Google Scholar
2 Irie T. Izawa M. Kurosawa E. Tetrahedron 1970, 26: 851

Crossref Google Scholar
3 Fukuzawa A. Kurosawa E. Tetrahedron Lett. 1979, 32: 2797

Google Scholar
4 Watanabe K. Umeda K. Miyakado M. Agric. Biol. Chem. 1989, 53: 2513

Google Scholar
5 Kulkarni SK. Kurosawa E. Indian. J. Exp. Biol. 1981, 19: 101

Google Scholar
6a Fukuzawa A. Aye M. Takasugi Y. Nakamura M. Tamura M. Murai A. Chem. Lett. 1994, 2307

Crossref Google Scholar
6b Ishihara J. Shimada Y. Kanoh N. Takasugi Y. Fukuzawa A. Murai A. Tetrahedron 1997, 53: 8371

Crossref Google Scholar
7 For the first total syntheses of 1 and 4, see: Crimmins MT. Tabet EA. J. Am. Chem. Soc. 2000, 122: 5473

Crossref Google Scholar
For recent reviews on olefin metathesis, see:
8a Grubbs RH. Miller SJ. Fu GC. Acc. Chem. Res. 1995, 28: 446

Google Scholar
8b Schuster M. Blechert S. Angew. Chem., Int. Ed. Engl. 1997, 36: 2067 ; Angew. Chem. 1997, 109, 2124

Google Scholar
8c Grubbs RH. Chang S. Tetrahedron 1998, 54: 4413

Google Scholar
8d Armstrong SK. J. Chem. Soc., Perkin Trans. 1 1998, 371

Google Scholar
8e Blechert S. Pure Appl. Chem. 1999, 71: 1393

Google Scholar
8f Fürstner A. Angew. Chem. Int. Ed. 2000, 39: 3013

Google Scholar
9 For a recent review on cyclic ethers, see: Elliot MC. J. Chem. Soc., Perkin Trans. 1 1998, 4175

Crossref Google Scholar
10a Uenishi J. Kawahama R. Yonemitsu O. Tsuji J. J. Org. Chem. 1996, 61: 5716

Crossref Google Scholar
10b Uenishi J. Kawahama R. Yonemitsu O. Tsuji J. J. Org. Chem. 1998, 63: 8965

Crossref Google Scholar
10c See, also: Fujiwara K. Awakura D. Tsunashima M. Nakamura A. Honma T. Murai A. J. Org. Chem. 1999, 64: 2616

Crossref Google Scholar
11 Another approach to cyclize a triene precursor into a medium-sized cyclic ether by RCM has been reported, where the modest selectivity has been observed: Crimmins MT. Emmitte KA. Choy AL. Tetrahedron 2002, 58: 1817

Crossref Google Scholar
12 Giannis A. Sandhoff K. Tetrahedron Lett. 1985, 26: 1479

Crossref Google Scholar
13a Omura K. Swern D. Tetrahedron 1978, 34: 1651

Article in Thieme Connect Google Scholar
13b Mancuso AJ. Huang S.-L. Swern D. J. Org. Chem. 1978, 43: 2480

Article in Thieme Connect Google Scholar
13c Mancuso AJ. Swern D. Synthesis 1981, 165

Article in Thieme Connect Google Scholar
14 Henry KJ. Grieco PA. Jagoe CTJ. Tetrahedron Lett. 1992, 33: 1817

Crossref Google Scholar
15a Shimizu T. Hiranuma S. Nakata T. Tetrahedron Lett. 1996, 37: 6145

Article in Thieme Connect Google Scholar
15b Shimizu T. Ohzeki T. Hiramoto K. Hori N. Nakata T. Synthesis 1999, 1373

Article in Thieme Connect Google Scholar
16a Hooz J. Gilani SSH. Can. J. Chem. 1968, 46: 86

Crossref Google Scholar
16b Murai A. Murase H. Matsue H. Masamune T. Tetrahedron Lett. 1977, 2507

Crossref Google Scholar
16c Tsushima K. Murai A. Tetrahedron Lett. 1992, 33: 4345

Crossref Google Scholar
17a Schmidt SP. Brooks DW. Tetrahedron Lett. 1987, 28: 767

Article in Thieme Connect Google Scholar
17b Brats M. Bullock WH. Overman LE. Takemoto T. J. Am. Chem. Soc. 1995, 117: 5958

Article in Thieme Connect Google Scholar
17c See, also: Fujiwara K. Kobayashi M. Awakura D. Murai A. Synlett 2000, 1187

Article in Thieme Connect Google Scholar
18 Scholl M. Ding S. Lee CW. Grubbs RH. Org. Lett. 1999, 1: 953

Google Scholar
19 Fu GC. Nguyen ST. Grubbs RH. J. Am. Chem. Soc. 1993, 115: 9856

Google Scholar
20 Sonogashira K. Tohda Y. Hagihara N. Tetrahedron Lett. 1975, 4467

Crossref Google Scholar