RSS-Feed abonnieren
DOI: 10.1055/s-2002-19289
Syntheses of Oxetanocin A and Related Unusual Nucleosides with Bis(hydroxymethyl)-branched Sugars
Publikationsverlauf
Publikationsdatum:
04. August 2004 (online)
![](https://www.thieme-connect.de/media/synthesis/200201/lookinside/thumbnails/10.1055-s-2002-19289-1.jpg)
Abstract
Since the naturally occurring unusual nucleoside oxetanocin A and its derivatives have been found to be effective as anti-HIV-1 and anti-herpes virus agents in 1986, the syntheses of different types of sugar-modified nucleoside analogs have been reported. In this review we will give an overview of the efforts to synthesize oxetanocin A from the first synthesis in 1987 and the related unusual nucleosides with bis(hydroxymethyl)-branched sugars, including our works in this area.
1 Introduction
2 Total Synthesis of Oxetanocin A
2.1 Nippon Kayaku’s Synthesis
2.2 Abbott’s Synthesis
2.3 Yamamura’s Synthesis
2.4 Fleet’s Synthesis
2.5 Just’s Synthesis
3 Practical Synthesis of 1-O-Acetyloxetanose Derivatives
4 Chemical Reactivity and Transformation of OXT-A
4.1 Enzymatic Transformation of OXT-A
4.2 Chemical Reactivity of OXT-A
4.3 Alkylphosphonic Acid Derivatives of OXT-A
5 Oxetanosyl C-Nucleosides
5.1 Re-examination of Ring Transformation
5.2 Synthesis of C-Oxetanosyl Nucleosides
5.2.1 Synthesis of C-Oxetanosyl Maleimide
5.2.2 Synthesis of C-Oxetanosyl Thiazole
6 Carbocyclic Analogs of OXT-A
6.1 Honjo’s Synthesis
6.2 Narasaka’s Synthesis
6.3 Squibb’s Synthesis
6.4 Abbott’s Synthesis (I)
6.5 Kaneko’s Synthesis
6.6 Abbott’ Synthesis (II)
6.7 Bristol-Meyers-Squibb’s Synthesis
6.8 Robert’s Synthesis
6.9 Kato’s Synthesis
6.10 Jung’s Synthesis
6.11 Taguchi’s Synthesis
6.12 Somekawa’s Synthesis
6.13 Hegedus’ Synthesis
7 Thietanosyl Nucleosides
8 Azetidinyl Nucleosides
9 Nucleosides with Bis(hydroxymethyl)-branched Sugars
9.1 Cyclopropyl Carbocyclic Nucleosides
9.2 Ring-enlarged OXT-A Analogs
9.3 Ring-enlarged COXT-A Analogs
9.4 4"-Thionucleoside Analogs
9.5 Miscellaneous
10 Conclusions
Key words
nucleobases - nucleosides - glycosidation - heterocycles - total synthesis
-
2a
Shimada N.Hasegawa S.Harada T.Tomisawa T.Fujii A.Takita T. J. Antibiot. 1986, 39: 1623 -
2b
Nakamura H.Hasegawa S.Shimada N.Fujii A.Takita T.Iitaka Y. J. Antibiot. 1986, 39: 1629 - 3
Hoshino H.Shimizu N.Shimada N.Takita T.Takeuchi T. J. Antibiot. 1987, 40: 1077 - 4
Huryn DN.Okabe M. Chem. Rev. 1992, 92: 1745 - 5
Borthwick AD.Biggadike K. Tetrahedron 1992. 48: p.571 - 6
Agrofoglio LA.Suhas E.Farese A.Condom R.Challand SR.Earl RA.Guedj R. Tetrahedron 1994. 36: p.10611 - 7
Crimmins MT. Tetrahedron 1998, 54: 9229 - 8
Ichikawa E.Kato K. Curr. Med. Chem. 2001, 8: 385 - 9
Bird CW.Thomas J. Chem. Ind. (London) 1985, 600 - 10
Ichikawa Y.Niitsuma S.Kato K.Takita T. J. Chem. Soc., Chem. Commun. 1988, 625 -
11a
Niitsuma S.Ichikawa Y.Kato K.Takita T. Tetrahedron Lett. 1987, 28: 3967 -
11b
Niitsuma S.Ichikawa Y.Kato K.Takita T. Tetrahedron Lett. 1987, 28: 4713 - 12
Gelas J.Horton D. Carbohydr. Res. 1975, 45: 181 - 13
Norbeck DW.Kramer JB. J. Am. Chem. Soc. 1988, 110: 7217 - 14
Robins MJ.Hansske F.Low NH.Park JI. Tetrahedron Lett. 1984, 25: 367 - 15
Cavender CJ.Shiner VJ. J. Org. Chem. 1972, 37: 3567 -
16a
Nishiyama S.Yamamura S.Kato K.Takita T. Tetrahedron Lett. 1988, 29: 4739 -
16b
Nishiyama S.Yamamura S.Kato K.Takita T. Tetrahedron Lett. 1988, 29: 4743 - 17
Acton EM.Goerner RN.Uh HS.Ryan KJ.Henry DW.Cass CE.LePage GA. J. Med. Chem. 1979, 22: 518 - 18
Tius MA.Faug H. J. Org. Chem. 1983, 48: 4132 - 19
Wilson FX.Fleet GWJ.Vogt K.Wang Y.Witty DR.Choi S.Storer R.Meyers PL.Wallis CJ. Tetrahedron Lett. 1990, 31: 6931 - 20
Barton DHR.Crich D.Motherwell WD. Tetrahedron 1985, 41: 3901 - 21
Hambalek R.Just G. Tetrahedron Lett. 1990, 38: 5445 - 22
Vorbrüggen H.Krolikiewicz K.Bennua B. Chem. Ber. 1981, 114: 1234 -
23a
Nagai M.Kato K.Takita T.Nishiyama S.Yamamura S. Tetrahedron Lett. 1990, 31: 119 -
23b
Nishiyama S.Yamamura S.Kato K.Nagai M.Takita T.Terada Y. Tetrahedron Lett. 1990, 31: 4777 -
23c
Nagai M.Kato K.Takita T.Nishiyama S.Yamamura S. Tetrahedron 1990, 46: 7703 -
24a
Shimada N.Hasegawa S.Saito S.Nishikiori T.Fujii A.Takita T. J. Antibiot. 1987, 40: 1788 -
24b
Masuda A.Kitagawa M.Tanaka A.Saito S.Shimada N.Ikeda R.Hoshino H.Daikoku T.Hishiyama Y. J. Antibiot. 1993, 46: 1034 -
25a
Kato K.Minami T.Takita T.Nishiyama S.Yamamura S.Naganawa H. Tetrahedron Lett. 1989, 30: 2269 -
25b
Kato K.Minami T.Takita T.Nishiyama S.Ohgiya T.Yamamura S. J. Chem. Soc., Chem. Commun. 1989, 1037 -
26a
De Clercq E.Holy A.Rosenberg I.Sakuma T.Balzarini J.Maudgal PC. Nature 1986, 323: 464 -
26b
Bronson JJ.Ghazouli I.Hitchcock MJM.Webb RR.Martin JC. J. Med. Chem. 1989, 32: 1457 - 27
Ogino Y.Nishiyama S.Yamamura S.Izawa T.Kato K. Bioorg. Med. Chem. Lett. 1994, 4: 1991 - 28
Barton DHR.Gero SD.Quiclet-Sire B.Samadi M. Tetrahedron 1992, 48: 1627 - 29
Izawa T.Nakayama K.Nishiyama S.Yamamura S.Kato K.Takita T. J. Chem. Soc., Perkin Trans.1 1992, 3003 - 30
Watanabe T.Nishiyama S.Yamamura S.Kato K.Nagai M.Takita T. Tetrahedron Lett. 1991, 32: 2399 - 31
Kikuchi Y.Nishiyama S.Yamamura S.Kato K.Fujiwara S.Umezawa K.Terada Y. Bioorg. Med. Chem. Lett. 1996, 6: 1897 - 32
Norbeck D.Kern E.Hayashi S.Rosenbrook W.Sham HL.Herrin T.Plattner JJ.Erickson J.Clement J.Swanson R.Shiplowitz H.Hardy D.Marsh K.Anett G.Shannon W.Broder S.Mitsuya H. J. Med. Chem. 1990, 33: 1281 - 33
Honjo M.Maruyama T.Sato Y.Horii T. Chem. Pharm. Bull. 1989, 37: 1413 - 34
Brannock KC.Burpitt RD.Thweatt JG. J. Org. Chem. 1964, 29: 940 - 35
Ichikawa Y.Narita A.Shiozawa A.Hayashi Y.Narasaka K. J. Chem. Soc., Chem. Commun. 1989, 1919 - 36
Corey EJ.Erickson BW. J. Org. Chem. 1971, 36: 3553 - 37
Slusarchyk WA.Young MG.Bisacchi GS.Hockstein DR.Zahler R. Tetrahedron Lett. 1989, 47: 6453 - 38
Hsiao C.-N.Hannick SM. Tetrahedron Lett. 1990, 46: 6609 -
39a
Wenger R. Helv. Chim. Acta 1983, 66: 2308 -
39b
Nicolaou KC.Papahatijs DP.Claremon DA.Magolda RL.Dolle RE. J. Org. Chem. 1985, 50: 1440 - 40
Hsiao C.-N.Shechter H. J. Org. Chem. 1988, 53: 2688 - 41
Kocienski PJ. J. Org. Chem. 1980, 45: 2307 - 42
Trost BM.Bogdanowicz MJ. J. Am. Chem. Soc. 1971, 93: 3773 - 43
Blomquist AT.Longone DT. J. Am. Chem. Soc. 1959, 81: 2012 - 44
von Doering WE.Roth HD. Tetrahedron 1970, 26: 2825 - 45
Katagiri N.Sato H.Kaneko C. Chem. Pharm. Bull. 1990, 38: 288 - 46
Ahmad S. Tetrahedron Lett. 1991, 32: 6997 -
47a
Furuta K.Iwanaga K.Yamamoto H. Tetrahedron Lett. 1986, 27: 4507 -
47b
Corey EJ.Wei-guo S. Tetrahedron Lett. 1988, 29: 3423 - 48
Cotterill IC.Roberts SM. J. Chem. Soc., Perkin Trans. 1 1992, 2585 - 49
Huisgen R.Otto R. Chem. Ber. 1969, 102: 3475 - 50
Cotterill IC.Sutherland AG.Roberts SM.Grobbauer R.Spreitz J.Farber K. J. Chem. Soc., Perkin Trans. 1 1991, 1365 - 51
Davies HG.Rahman SS.Roberts SM.Wakeefield BJ.Winders JA. J. Chem. Soc., Perkin Trans. 1 1987, 85 - 52
Izawa T.Ogino Y.Nishiyama S.Yamamura S.Kato K.Takita T. Tetrahedron 1992, 48: 1573 - 53
Misumi A.Iwanaga K.Furuta K.Yamamoto H. J. Am. Chem. Soc. 1985, 107: 3343 - 54
Jung ME.Sledeski AW. J. Chem. Soc., Chem. Commun. 1993, 589 - 55
Brauman JI.Archie WC. J. Am. Chem. Soc. 1972, 94: 4262 - 56
Robins MJ.Wilson JS.Hansske F. J. Am. Chem. Soc. 1983, 105: 4059 - 57
Ito H.Motoki Y.Taguchi T.Hanzawa Y. J. Am. Chem. Soc. 1993, 115: 8835 - 58
Ito H.Taguchi T.Hanzawa Y. Tetrahedron Lett. 1993, 34: 7639 - 59
Somekawa K.Hara R.Kinnami K.Muraoka F.Suishu T.Shimo T. Chem. Lett. 1995, 407 - 60
Brian B.Hegedus LS. J. Org. Chem. 1998, 63: 8012 - 61
Reed AD.Hegedus LS. Organometallics 1997, 16: 2313 - 62
Furukawa S.-I.Tsuchimoto T. Tetrahedron Lett. 1995, 36: 5937 - 63
Petasis NA.Bzowej EI. J. Am. Chem. Soc. 1990, 112: 6392 - 64
Hibino J.Okazoe T.Takai K.Nozaki H. Tetrahedron Lett. 1985, 26: 5579 - 65
Nishizono N.Koike N.Yamagata Y.Fujii S.Matsuda A. Tetrahedron Lett. 1996, 37: 7569 - 66
O’Neil IA.Hamilton KM. Synlett 1992, 791 - 67
Ichikawa E.Yamamura S.Kato K. Tetrahedron Lett. 1999, 40: 7385 -
68a
Hosono F.Nishiyama S.Yamamura S.Izawa T.Kato K. Bioorg. Med. Chem. Lett. 1994, 4: 2083 -
68b
Hosono F.Nishiyama S.Yamamura S.Izawa T.Kato K.Terada Y. Tetrahedron 1994, 50: 13335 -
68c
Nishiyama S.Kikuchi Y.Kurata H.Yamamura S.Izawa T.Nagahata T.Ikeda R.Kato K. Bioorg. Med. Chem. Lett. 1995, 5: 2273 -
69a
Nishiyama S.Ueki S.Watanabe T.Yamamura S.Kato K.Takita T. Tetrahedron Lett. 1991, 32: 2141 -
69b
Izawa T.Nishiyama S.Yamamura S.Kato K.Takita T. J. Chem. Soc., Perkin Trans. 1 1992, 2519 - 70
Heck RF. Org. React. 1982, 27: 345 - 71
Katagiri N.Sato H.Kaneko C. Chem. Pharm. Bull. 1990, 38: 3184 - 72
Rifé J.Ortuño RM. Org. Lett. 1999, 1: 1221 - 73
Pudlo JS.Townsend LB. Tetrahedron Lett. 1990, 31: 3101 - 74 See the review:
Wilson LJ.Hager MW.El-Kattan YA.Liotta D. Synthesis 1995, 1465 - 75
Svansson L.Kvarnström I.Classon B.Samuelsson B. J. Org. Chem. 1991, 56: 2993 - 76
Ashwell M.Jones AS.Walker RT. Nucleic Acids Res. 1987, 15: 2157 - 77
Faul MM.Huff BE.Dunlap SE.Frank SE.Fritz FE.Kaldor SW.LeTourneau ME.Staszak MA.Ward JA.Werner JA.Winneroski LL. Tetrahedron 1997, 53: 8085 - 78
Bamford MJ.Coe PL.Walker RT. J. Med. Chem. 1990, 33: 2494 - 79
Sanghvi YS.Bharadwaj R.Debart F.Mesmaeker AD. Synthesis 1994, 1163 - 80
Kaldor SW.Fritz JE.Ward JA. Tetrahedron Lett. 1997, 38: 1509 - 81
Garg N.Plavec J.Chattopadhyara J. Tetrahedron 1993, 49: 5189 - 82
Tseng CK.-H.Marquez VE.Milne GWA.Wysocki RJ.Mitsuya H.Shirasaki T.Driscoll JS. J. Med. Chem. 1991, 34: 343 - 83
Pavey JBJ.Lawrence AJ.Potter AJ.Cosstick R.O’Neil IA. Tetrahedron Lett. 1998, 39: 6967 - 84
Rosenquist Å;.Kvarnström I.Svensson SCT.Classon B.Samuelsson B. J. Org. Chem. 1994, 59: 1779 - 85
Rosenquist Å.Kvarström I.Svensson SCT.Classon B.Samuelsson B. Acta Chem. Scand. 1992, 46: 1127 - 86
Katagiri N.Nomura M.Sato H.Kaneko C.Yusa K.Tsuruo T. J. Med. Chem. 1992, 38: 4795 - 87
Moon HR.Kim HO.Chun MW.Jeong LS.Marquez VE. J. Org. Chem. 1999, 64: 4733 - 88
Marquez VE.Lim M.-I.Tseng CK.-H.Markovac A.Priest MA.Khan MS.Kaskar B. J. Org. Chem. 1988, 53: 5709 -
89a
Brånalt J.Kvarnström I.Niklasson G.Svensson SCT.Classon B.Samuelsson B. J. Org. Chem. 1994, 59: 1783 -
89b
Brånalt J.Kvarnström I.Svensson SCT.Classon B.Samuelsson B. J. Org. Chem. 1994, 59: 4430 - 90
Mann J.Tench AJ.Weymouth-Wilson AC.Shaw-Ponter S.Young RJ. J. Chem. Soc., Perkin Trans. 1 1995, 677 - 91
Ichikawa E.Yamamura S.Kato K. Bioorg. Med. Chem. Lett. 1999, 9: 1113 - 92
Kikuchi Y.Kurata H.Nishiyama S.Yamamura S.Kato K. Tetrahedron Lett. 1997, 38: 4795 - 93
Oohashi T.Nishiyama S.Yamamura S.Kato K. Bioorg. Med. Chem. Lett. 1998, 8: 1187 - 94
Tino JA.Clark JM.Field AK.Jacobs GA.Lis KA.Michalik TL.McGeever-Rubin B.Slusarchyk WA.Spergel SH.Sundeen JE.Tuomari AV.Weaver ER.Young MG.Zahler R. J. Med. Chem. 1993, 36: 1221 - 95
Jung ME.Nichols CJ. J. Org. Chem. 1998, 63: 347 - 96
Brånalt J.Kvarnström I.Classon B.Samuelsson B. J. Org. Chem. 1996, 61: 3599 - 97
Brånalt J.Kvarnström I.Classon B.Samuelsson B. J. Org. Chem. 1996, 61: 3604 - 98
Kolb HC.Van Nieuwenhze MS.Sharpless KB. Chem. Rev. 1994, 94: 2483 - 99
Brånalt J.Kvarnström I.Classon B.Samuelsson B. J. Org. Chem. 1996, 61: 3611 - 100
Chao Q.Nair V. Bioorg. Med. Chem. Lett. 1997, 7: 1199
References
Current address: Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.