A New Access to 16-Membered
Macrocycles: Synthesis of the Model C-O-D
Ring System of Vancomycin

Samir Ghosh; A. Sanjeev Kumar; G. N. Mehta; R. Soundararajan

doi:10.1055/s-0029-1216937

PAPER

A New Access to 16-Membered Macrocycles: Synthesis of the Model C-O-D Ring System of Vancomycin

Samir Ghosh^a, A. Sanjeev Kumar^a, G. N. Mehta^b, R. Soundararajan*^a
^a Chemical Research and Development Department, Pfizer Ltd., Mumbai 400705, India
Fax: +91(22)67932444; e-Mail: soundara1959@yahoo.com;
^b Applied Chemistry Department, S. V. National Institute of Technology, Surat 395007, India

Abstract

All articles of this category

Abstract

A simple methodology for construction of the C-O-D diphenyl ether 16-membered ring system present in vancomycin by an intramolecular O-arylation reaction of arylboronic acid with substituted phenol for formation of the macrocyclic biaryl ether is described.

Key words

vancomycin - antibiotics - arylboronate - ring closure - O-arylation

Full Text

References

1 Glycopeptide Antibiotics Nagarajan R. Marcel Dekker; New York: 1994.

2a Sheldrick GM. Jones PG. Kennard O. Williams DH. Smith GA. Nature (London) 1978, 271: 223

2b Loll PJ. Bevivino AE. Korty BD. Axelson PH. J. Am. Chem. Soc. 1997, 119: 1516

2c McCormick MH. Stark WM. Pittenger RC. McGuire GM. Antibiot. Annu. 1955-1956, 606

2d Harris CM. Harris TM. J. Am. Chem. Soc. 1982, 104: 4293

2e Harris CM. Kopecka H. Harris TM. J. Am. Chem. Soc. 1983, 105: 6915

For reviews in the area, see:

3a Rao AVR. Gurjar MK. Reddy KL. Rao AS. Chem. Rev. 1995, 95: 2135

3b Burgess K. Lim D. Martinez CI. Angew. Chem. 1996, 108: 1162

3c Zhu JP. Synlett 1997, 133

4a Williamson MP. Williams DH. J. Am. Chem. Soc. 1981, 103: 6580

4b Nagarajan R. J. Antibiot. 1993, 46: 1181

5 Courvalin P. Antimicrob. Agents Chemother. 1990, 34: 2291

6 Malabarba A. Ciabatti R. J. Med. Chem. 1994, 37: 2988

7 Bois-Choussy M. Beugelmans R. Bouillon JP. Zhu J. Tetrahedron Lett. 1995, 36: 4781

8 Suzuki Y. Nishiyama S. Yamamura S. Tetrahedron Lett. 1989, 30: 6043

9 Evans DA. Ellman JA. DeVries KM. J. Am. Chem. Soc. 1989, 111: 8912

10a Griffith RS. J. Antimicrob. Chemother., Suppl. D 1984, 14: 1

10b Williams DH. Kalman JR. J. Am. Chem. Soc. 1977, 99: 2768

11 Evans DA. Watson PS. Tetrahedron Lett. 1996, 37: 3251

12 Hitotsuyanagi Y. Ishikawa H. Naito S. Takeya K. Tetrahedron Lett. 2003, 44: 5901

13 Rescek DM. Woodworth GF. Morgan BP. Coe JW. J. Org. Chem. 1999, 64: 9719

14 Morgan BJ. Xie X. Phuan P.-w. Kozlowski MC. J. Org. Chem. 2007, 72: 6171