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Synthesis 2012; 44(24): 3797-3804
DOI: 10.1055/s-0032-1317544
DOI: 10.1055/s-0032-1317544
paper
Synthetic Studies towards NG-121: Diastereoselective Synthesis of NG-121 Methyl Ether
Further Information
Publication History
Received: 27 September 2012
Accepted after revision: 19 October 2012
Publication Date:
31 October 2012 (online)
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Abstract
Starting from unsymmetrically O-protected methyl 4-bromo-3,5-dihydroxybenzoate, a facile synthesis of the methyl ether of bioactive natural product NG-121 was accomplished in very good overall yield. The key steps were: Stille coupling reaction of the farnesyl unit with the electron-rich phenolic segment; hydroxy-directed selective epoxidation of the farnesyl chain along with concomitant phenol-driven intramolecular regio- and diastereoselective ring closure to the corresponding hydroxybenzopyran; and regioselective formylation followed by in situ reductive lactonization.
Key words
4-bromo-3,5-dihydroxybenzoate - Stille coupling - intramolecular cyclization - formylation - lactonization - NG-121 methyl etherSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1 Nicolaou KC, Evans RM, Roecker AJ, Hughes R, Downes M, Pfefferkorn JA. Org. Biomol. Chem. 2003; 1: 908; and references cited therein
- 2a Orii Y, Ito M, Mizoue K, Mizobe F, Sakai N, Hanada K. JP 05,176,782 1993 ; Chem. Abstr. 1993, 119, 179349.
- 2b Nozawa Y, Yamamoto K, Ito M, Sakai N, Mizoue K, Mizobe F, Hanada K. J. Antibiot. 1997; 50: 635
- 3 Xu X, de Guzman FS, Gloer JB. J. Org. Chem. 1992; 57: 6700
- 4a Hasegawa K, Koide H, Hu W, Nishimura N, Narasaki R, Kitano Y, Hasumi K. J. Antibiot. 2010; 63: 589
- 4b Hasumi K, Hasegawa K, Kitano Y. J. Antibiot. 2007; 60: 463
- 5 Inoue S, Nakagawa C, Hayakawa H, Iwasaki F, Hoshino Y, Honda K. Synlett 2006; 1363
- 6 Inoue S, Kim R, Hoshino Y, Honda K. Chem. Commun. 2006; 1974
- 7a Mondal M, Argade NP. Tetrahedron Lett. 2004; 45: 5693
- 7b Mondal M, Argade NP. Synlett 2004; 1243
- 7c Mondal M, Puranik VG, Argade NP. J. Org. Chem. 2006; 71: 4992
- 7d Mondal M, Puranik VG, Argade NP. J. Org. Chem. 2007; 72: 2068
- 7e Singh M, Argade NP. J. Org. Chem. 2010; 75: 3121
- 8 Lindgren BO, Nilsson T. Acta Chem. Scand. 1973; 27: 888
- 9a Lee AS. Y, Hu YJ, Chu SF. Tetrahedron 2001; 57: 2121
- 9b Li Y, Luo Y, Huang W, Wang J, Lu W. Tetrahedron Lett. 2006; 47: 4153
- 10 Lattanzi A, Scettri A. Synlett 2002; 942
- 11a Takemura S, Hirayama A, Tokunaga J, Kawamura F, Inagaki K, Hashimoto K, Nakata M. Tetrahedron Lett. 1999; 40: 7501
- 11b Jung YS, Joe BY, Seong CM, Park NS. Bull. Korean Chem. Soc. 2000; 21: 463
- 11c Takaoka S, Nakade K, Fukuyama Y. Tetrahedron Lett. 2002; 43: 6919
- 12 Littke AF, Schwarz L, Fu GC. J. Am. Chem. Soc. 2002; 124: 6343
- 13 Inoue S, Asami M, Honda K, Shrestha KS, Takahashi M, Yoshino T. Synlett 1998; 679
- 14a Jung ME, Lyster MA. J. Org. Chem. 1977; 42: 3761
- 14b Bernard AM, Ghiani MR, Piras PP, Rivoldini A. Synthesis 1989; 287
- 14c Saimoto H, Hiyama T. Tetrahedron Lett. 1986; 27: 597
- 14d Taishi T, Takechi S, Mori S. Tetrahedron Lett. 1998; 39: 4347
- 14e Gevorgyan V, Liu JX, Rubin M, Benson S, Yamamoto Y. Tetrahedron Lett. 1999; 40: 8919