Synthesis, Inhaltsverzeichnis PAPER © Georg Thieme Verlag Stuttgart · New York A Simple and Efficient Synthesis of 3′-Azido-3′-deoxythymidine (AZT) Employing a Convergent Route Bhaskar Dhotare, Angshuman Chattopadhyay*Bio-Organic Division, Bhabha Atomic Research Centre Mumbai-400,085, India Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract The syn-homoallyl alcohol 2a has been prepared with absolute stereoselectivity following PDC oxidation of the mixture of diastereomers 2a, 2b and subsequent K-selectride® reduction of the resulting ketone 3. Compound 2a has been efficiently utilized for a simple synthesis of AZT I in a convergent manner. Key words AIDS - convergent synthesis - (R)-2,3-O-cyclohexylideneglyceraldehyde - K-selectride - syn selective reduction - open chain model - flexibility Volltext Referenzen References 1a Huryn DM. Okabe M. Chem. Rev. 1992, 92: 1745 ; and references cited therein 1b Dueholm KL. Pedersen EB. Synthesis 1992, 1 ; and references cited therein 1c Lipshutz BH. Hayawaka H. Kato K. Lowe RF. Synthesis 1994, 1476 ; and references cited therein 1d Wilson LJ. Hager MW. El-Kattan YA. Liotta DC. Synthesis 1995, 1465 ; and references cited therein 1e Jung ME. Nichols CJ. J. Org. Chem. 1998, 63: 347 1f Shuto S. Kanazaki M. Ichikawa S. Minakawa N. Matsuda A. J. Org. Chem. 1998, 63: 746 1g Sorensen MD. Khalifa NM. Pedersen EB. Synthesis 1999, 1937 2 DeClercq E. Collect. Czech. Chem. Commun. 1998, 63: 449 3a Mitsua H. Yarchoan R. Broder S. Science 1990, 249: 1533 3b DeClerq E. Nucleosides, Nucleotides 1994, 13: 1271 3c DeClerq E. J. Med. Chem. 1995, 38: 2491 3d Mansour TS. Storer R. Current Pharmac. Design 1997, 3: 227 3e New medicines in Development of AIDS, available at http://www.pharma.org. 4a Fleet GWJ. Son JC. Derome AE. Tetrahedron 1988, 44: 625 4b Gurjar MK. Pawar SM. Rama Rao AVJ. J. Carbohydr. Chem. 1988, 7: 271 4c Chu CK. Beach WJ. Ullas GV. Kosugi Y. Tetrahedron Lett. 1988, 29: 5349 4d Hansen P. Pedersen EB. Acta Chem. Scand. 1990, 44: 522 4e Sugimura H. Osumi K. Yamazaki T. Yamaya T. Tetrahedron Lett. 1991, 32: 1813 5a Hager MW. Liotta DC. J. Am. Chem. Soc. 1991, 113: 5117 5b Jung ME. Gardiner JM. J. Org. Chem. 1991, 56: 2614 5c Chen B. Quinlan SL. Read SG. Tetrahedron Lett. 1995, 36: 7691 5d Mandal SB. Achari B. J. Chem. Res., Synop. 1993, 327 ; and references cited therein 5e Sigmund H. Pfleiderer W. Helv. Chim. Acta 1996, 79: 426 6a Chattopadhyay A. Mamdapur VR. J. Org. Chem. 1995, 60: 585 6b Chattopadhyay A. J. Org. Chem. 1996, 61: 6104 6c Chattopadhyay A. Tetrahedron: Asymmetry 1997, 8: 2727 7 Corey EJ. Schmidt G. Tetrahedron Lett. 1979, 399 8a Sato F. Kobayashi O. Chiba T. Takeda Y. Kasakabe M. J. Chem. Soc., Chem. Commun. 1985, 1636 8b Roush WR. Walts AE. Hong LK. J. Am. Chem. Soc. 1985, 107: 8186 8c Dondoni A. Fantin G. Fogagnoto M. Medici A. Pedrini P. J. Org. Chem. 1989, 54: 702 8d Dondoni A. Synthesis 1998, 1681 ; and references cited therein 8e Dehoux C. Mothien C. Baltas M. Gorricon L. Synthesis 2000, 1409 9a Cherest M. Felkin H. Prudent N. Tetrahedron Lett. 1968, 2199 9b Oishi T. Nakata T. Acc. Chem. Res. 1984, 17: 338 9c Nakata T. Tanaka T. Oishi T. Tetrahedron Lett. 1983, 2653 9d Mengel A. Reiser O. Chem. Rev. 1999, 99: 1191 ; and references cited therein 10 Grauert M. Schollkopf U. Liebigs Ann. Chem. 1985, 1817
