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-00000084.xml
Synthesis 2016; 48(23): 4167-4174
DOI: 10.1055/s-0035-1562787
DOI: 10.1055/s-0035-1562787
paper
An Asymmetric Synthesis of Rosuvastatin Calcium
Further Information
Publication History
Received: 15 April 2016
Accepted after revision: 20 June 2016
Publication Date:
16 August 2016 (online)
Abstract
A novel asymmetric synthesis of a (3R,5S)-dihydroxyhexanoic ester is described. The ester, which serves as the precursor for generating the side chain of rosuvastatin, is synthesized from d-glucose and subsequently coupled, under Wittig olefination conditions, with a phosphonium ylide derived from an appropriately substituted pyrimidine moiety. The coupling results in the formation of a precursor containing all the structural features of rosuvastatin. This precursor is converted into rosuvastatin calcium following a well-established procedure.
Key words
total synthesis - rosuvastatin calcium - Wittig olefination - lactone reduction - diastereoselective reduction - sugar chemistry - d-glucoseSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562787.
- Supporting Information
-
References
- 1 Pfefferkorn JA In The Art of Drug Synthesis . Johnson DS, Li J. John Wiley & Sons; Hoboken: 2007: 169-182
- 2 Casar Z. Curr. Org. Chem. 2010; 14: 816
- 3a Hirai K, Ishiba T, Koika H, Watanabe M. US Patent 5260440, 1993
- 3b Watanabe M, Koika H, Ishiba T, Okada T, Seo S, Hirai K. Bioorg. Med. Chem. 1997; 5: 437
- 4a Konoike T, Araki Y. J. Org. Chem. 1994; 59: 7849
- 4b Theisen PD, Heathcock CH. J. Org. Chem. 1988; 53: 2374
- 4c Korostylev A, Andrushko V, Andrushko N, Tararov VI, König G, Börner A. Eur. J. Org. Chem. 2008; 840
- 5a Narasaka K, Pai CH. Chem. Lett. 1980; 9: 1415
- 5b Chen KM, Gunderson KG, Hardtmann GE, Prasad K, Repic O, Shapiro MJ. Chem. Lett. 1987; 16: 1923
- 5c Chen KM, Hardtmann GE, Prasad K, Repic O, Shapiro MJ. Tetrahedron Lett. 1987; 28: 155
- 6a Diorazia LT, Kobaki M, Koika H, Taylor NP. WO 2000049014 A1, 2000
- 6b Joshi N, Bhirud S, Chandrasekhar B, Rao K, Damle S. US Patent 0124639 A, 2005
- 6c Anegondi SP, Rajmahendra S, Joseph J, Srinivas PV. WO 2010023678 A1, 2010
- 6d Pandya VP, Richhariya S, Divya P, Meeran HN. P. N, Tewari N. WO 2011132172 A1, 2011
- 6e Akio M, Mizuho O, Yasuhiro K, Junichi C. US Patent 7304156 B2, 2007
- 7a Hirai K, Ishiba T, Koika H, Watanabe M. EP0521471 B1, 2000
- 7b Diorazia LT, Kobaki M, Koika H, Taylor NP. WO 2000049014 A1, 2000
- 7c Creekmore JR, Wiggins NA. US Patent 6316460 B1, 2001
- 7d Okada T, Horbury J, Dermot D, Laffan P. WO 2005042522 A1, 2005
- 7e Horbury J, Taylor NP. US Patent 7511140, 2009
- 7f Reddy MS, Rajan ST, Reddy MS. US Patent 8455640 B2, 2013
- 7g Okada T, Horbury J, Laffan P. US Patent 0301348 A1, 2011
- 8a Wess G, Kesseler K, Baader E, Bartmann W, Beck G. DE 3741509 A1, 1988
- 8b Wess G, Kesseler K, Baader E, Bartmann W, Beck G, Bergmann A, Jendralla H, Bock K, Holzstein G, Kleine H, Schnierer M. Tetrahedron Lett. 1990; 31: 2545
- 8c Choi H, Shin H. Synlett 2008; 1523
- 8d Beck G, Jendralla H, Kesseler K. Synthesis 1995; 1014
- 8e Urabe H, Matsuka T, Sate F. Tetrahedron Lett. 1993; 33: 4183
- 8f Lee GT, Linder J, Chen KM, Prasad K, Repic O, Hardtmann GE. Synlett 1990; 508
- 8g Prasad K, Chen KM, Repic O, Hardtmann GE. Tetrahedron: Asymmetry 1990; 1: 307
- 8h Muller M. Angew. Chem. Int. Ed. 2005; 44: 362
- 9a Minami T, Hiyama T. Tetrahedron Lett. 1992; 33: 7525
- 9b Takahashi K, Minami T, Hiyama T. Tetrahedron Lett. 1993; 34: 513
- 9c Hiyama T, Minami T, Takahashi K. Bull. Chem. Soc. Jpn. 1995; 68: 364
- 9d Solladié G, Bauder C, Rossi L. J. Org. Chem. 1995; 60: 7774
- 9e Honda T, Ono S, Mizutani H, Hallinan KO. Tetrahedron: Asymmetry 1997; 8: 181
- 9f Shin HI, Choi BS, Lee KK, Choi H, Chang JH, Lee KW, Nam DH, Kim NS. Synthesis 2004; 2629
- 10 Apparao T, Ghosh PK, Pradhan BS, Rangarao Ch, Vempala N. WO 2012032534 A3, 2012
- 11 Humphlett WJ. Carbohydr. Res. 1967; 4: 157
- 12 Isbell HS. Methods Carbohydr. Chem. 1963; 2: 13
- 13 A similar type of β-elimination was observed in aldonolactones, see: Varela OJ, Cireli AF, De Lederkremer RM. Carbohydr. Res. 1979; 70: 27
- 14a Takahashi K, Minami T, Ohara Y, Hiyama T. Tetrahedron Lett. 1993; 34: 8263
- 14b Takahashi K, Minami T, Ohara Y, Hiyama T. Bull. Chem. Soc. Jpn. 1995; 68: 2649
- 15 Ding X, Wang W, Kong F. Carbohydr. Res. 1997; 303: 445
- 16 Kitamura M, Isobe M, Ichikawa Y, Goto T. J. Am. Chem. Soc. 1984; 106: 3252
- 17a Zemplén G, Kuntz A. Ber. Dtsch. Chem. Ges. 1924; 57B: 1357
- 17b Wang Z. Comprehensive Organic Name Reactions and Reagents. John Wiley & Sons; Hoboken: 2010: 3123-3128