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Synthesis 2013; 45(14): 1991-1996
DOI: 10.1055/s-0033-1338799
DOI: 10.1055/s-0033-1338799
paper
Total Synthesis of (+)-Pinellic Acid
Further Information
Publication History
Received: 08 March 2013
Accepted after revision: 18 April 2013
Publication Date:
17 May 2013 (online)
Abstract
A straightforward strategy for the synthesis of (+)-pinellic acid in 16% overall yield and 13 steps, starting from (1R)-1-(furan-2-yl)hexan-1-ol, is described. Key reactions in the synthesis include a Sharpless kinetic resolution, oxidation of a protected furan to reveal a but-2-ene-1,4-dione moiety, and an asymmetric reduction.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1 Funk CD, Powell WS. Biochim. Biophys. Acta 1983; 754: 57
- 2 Kato T, Yamaguchi Y, Abe N, Uyehara T, Namai T, Kodama M, Shiobara Y. Tetrahedron Lett. 1985; 26: 2357
- 3 Nagai T, Kiyohara H, Munakata K, Shirahata T, Sunazuka T, Harigaya Y, Yamada H. Int. Immunopharmacol. 2002; 2: 1183
- 4 Qiu Y, Zhao Y, Dou D, Xu B, Liu K. Arch. Pharm. Res. 2007; 30: 665
- 5 Choi J.-Y, Seo C.-S, Zheng M.-S, Lee C.-S, Son J.-K. Arch. Pharm. Res. 2008; 31: 1413
- 6 Sunazuka T, Shirahata T, Yoshida K, Yamamoto D, Harigaya Y, Nagai T, Kiyohara H, Yamada H, Kuwajima I, Ōmura S. Tetrahedron Lett. 2002; 43: 1265
- 7a Shirahata T, Sunazuka T, Yoshida K, Yamamoto D, Harigaya Y, Nagai T, Kiyohara H, Yamada H, Kuwajima I, Ōmura S. Bioorg. Med. Chem. Lett. 2003; 13: 937
- 7b Shirahata T, Sunazuka T, Yoshida K, Yamamoto D, Harigaya Y, Kuwajima I, Nagai T, Kiyohara H, Yamada H, Ōmura S. Tetrahedron 2006; 62: 9483
- 7c Naidu SV, Gupta P, Kumar P. Tetrahedron 2007; 63: 7624
- 7d Prasad KR, Swain B. Tetrahedron: Asymmetry 2008; 19: 1134
- 7e Miura A, Kuwahara S. Tetrahedron 2009; 65: 3364
- 7f Sabitha G, Bhikshapathi M, Reddy EV, Yadav JS. Helv. Chim. Acta 2009; 92: 2052
- 7g Sharma A, Mahato S, Chattopadhyay S. Tetrahedron Lett. 2009; 50: 4986
-
8 Kobayashi Y, Watatani K, Kikori Y, Mizojiri R. Tetrahedron Lett. 1996; 37: 6125
- 9a Kobayashi Y, Nakano M, Kumar GB, Kishihara K. J. Org. Chem. 1998; 63: 7505
- 9b Kobayashi Y, Matsuumi M. J. Org. Chem. 2000; 65: 7221
- 9c Kobayashi Y, Kumar GB, Kurachi T, Acharya HP, Yamazaki T, Kitazume T. J. Org. Chem. 2001; 66: 2011
- 10 Prasad KR, Pawar AB. Org. Lett. 2011; 13: 4252
- 11 Kusakabe M, Kitano Y, Kobayashi Y, Sato F. J. Org. Chem. 1989; 54: 2085
- 12 The configuration of the major diastereomer was assigned by analogy to similar reductions performed previously in our laboratory (see ref. 10). Also, see: Prasad KR, Gutala P. Tetrahedron 2011; 67: 4514
- 13 Noyori R, Tomino I, Tanimoto Y, Nishizawa M. J. Am. Chem. Soc. 1984; 106: 6709