Stereoisomers of 249 can be obtained readily, for instance, by exo-dihydroxylation
of (+)-170. As seen in Scheme 29, trans- and cis-aminohydroxylated derivatives
can be prepared also with high stereo- and regioselectivity, thus permitting, in
principle, the synthesis of aza-C-disaccharides containing amino-iminopentitols.
6 Conclusion
As other cyclic ethers, 7-oxabicyclo[2.2.1]heptanes (7-oxanorbornanes) and alkylsubstituted derivatives have been used to generate all kinds of polymers. A large
number of 7-oxanorbornanes are found in Nature, and many of them possess quite
interesting biological activities that have stimulated their total synthesis. The
7-oxanorbornane system is a molecular device for the construction of bioactive
compounds in which the pharmacophores have to occupy specific positions in
space. A large number of enantiomerically pure, or enantiomerically enriched,
7-oxanorbornanes are readily available and can be used to construct all kinds of
compounds of biological interest such as rare sugars and analogues and monosaccharide and disaccharide mimetics. The chemistry of 7-oxanorbornanes is quite rich
and generates a wide chemodiversity in a highly stereoselective manner.
References
1. Giusti P, Florentino U, Turchi G, Andruzzi F, Magagnini PL (1969) Makromol Chem 128:1
2. Stejny JJ (1973) Macromol Sci Chem 7:1435
3. Saegusa T, Motoi M, Suda H (1976) Macromolecules 9:231
4. Pretula L, Kaluzynski K, Szymanski R, Penczek S (1996) Macromolecules 29:6700
5. Pretula J, Kaluzynski K, Libiszowski J, Szymanski R, Penczek S (1997) J Polym Sci A Polym
Chem 35:1733
6. Bai RK, Li S-H, Zou Y-F, Pan C-Y, Uryu T (1994) Macromol Chem Phys 195:119
7. Bai R-K, Li S, Zou Y-F, Pan C-Y, Uryu T (1995) J Polym Sci A Polym Chem 33:1685
8. Buchlauer G, Holbick H (1991) Chemiker-Zeitung 115:141
9. Kita H, Nakaba H, Okoshi A, Watanabe S, Nakadaira K, Oki T, Noguchi J (2000) Jpn Kokai
Tokkyo Koho JP 2000128896 A 200000509
10. Maceina M, Slipke JW (2004) J Aquat Plant Manage 42:5
11. Vogel P, Cossy J, Plumet J, Arjona O (1999) Tetrahedron 55:13521
12. Schindler C, Carreira EM (2009) Chem Soc Rev 38:3222
13. Hrebabecky H, Dracinsky M, De Palma AM, Neyts J, Holy A (2009) Collect Czechoslov
Chem Commun 74:487
14. Castro CR, Dutler R, Rauk A, Wieser H (1987) J Mol Struct (Theochem) 152:241
15. Adkins H, Billica HR (1948) J Am Chem Soc 70:695
16. Fehnel EA, Goodyear S, Berkowitz J (1951) J Am Chem Soc 73:4978
17. Sikkema DJ, Hoogland P, Bik J, Lam PT (1986) Polymer 27:1441
18. Maegawa T, Akashi A, Yaguchi K, Iwasaki Y, Shigetsura YM, Sajiki H (2009) Chem Eur J
15:6953
19. Olberg RC, Pines H, Ipatieff VN (1943) J Am Chem Soc 65:2260
20. Pines H, Kobynski TP (1970) J Catal 17:394
182
A.J. Moreno-Vargas and P. Vogel
of (+)-170. As seen in Scheme 29, trans- and cis-aminohydroxylated derivatives
can be prepared also with high stereo- and regioselectivity, thus permitting, in
principle, the synthesis of aza-C-disaccharides containing amino-iminopentitols.
6 Conclusion
As other cyclic ethers, 7-oxabicyclo[2.2.1]heptanes (7-oxanorbornanes) and alkylsubstituted derivatives have been used to generate all kinds of polymers. A large
number of 7-oxanorbornanes are found in Nature, and many of them possess quite
interesting biological activities that have stimulated their total synthesis. The
7-oxanorbornane system is a molecular device for the construction of bioactive
compounds in which the pharmacophores have to occupy specific positions in
space. A large number of enantiomerically pure, or enantiomerically enriched,
7-oxanorbornanes are readily available and can be used to construct all kinds of
compounds of biological interest such as rare sugars and analogues and monosaccharide and disaccharide mimetics. The chemistry of 7-oxanorbornanes is quite rich
and generates a wide chemodiversity in a highly stereoselective manner.
References
1. Giusti P, Florentino U, Turchi G, Andruzzi F, Magagnini PL (1969) Makromol Chem 128:1
2. Stejny JJ (1973) Macromol Sci Chem 7:1435
3. Saegusa T, Motoi M, Suda H (1976) Macromolecules 9:231
4. Pretula L, Kaluzynski K, Szymanski R, Penczek S (1996) Macromolecules 29:6700
5. Pretula J, Kaluzynski K, Libiszowski J, Szymanski R, Penczek S (1997) J Polym Sci A Polym
Chem 35:1733
6. Bai RK, Li S-H, Zou Y-F, Pan C-Y, Uryu T (1994) Macromol Chem Phys 195:119
7. Bai R-K, Li S, Zou Y-F, Pan C-Y, Uryu T (1995) J Polym Sci A Polym Chem 33:1685
8. Buchlauer G, Holbick H (1991) Chemiker-Zeitung 115:141
9. Kita H, Nakaba H, Okoshi A, Watanabe S, Nakadaira K, Oki T, Noguchi J (2000) Jpn Kokai
Tokkyo Koho JP 2000128896 A 200000509
10. Maceina M, Slipke JW (2004) J Aquat Plant Manage 42:5
11. Vogel P, Cossy J, Plumet J, Arjona O (1999) Tetrahedron 55:13521
12. Schindler C, Carreira EM (2009) Chem Soc Rev 38:3222
13. Hrebabecky H, Dracinsky M, De Palma AM, Neyts J, Holy A (2009) Collect Czechoslov
Chem Commun 74:487
14. Castro CR, Dutler R, Rauk A, Wieser H (1987) J Mol Struct (Theochem) 152:241
15. Adkins H, Billica HR (1948) J Am Chem Soc 70:695
16. Fehnel EA, Goodyear S, Berkowitz J (1951) J Am Chem Soc 73:4978
17. Sikkema DJ, Hoogland P, Bik J, Lam PT (1986) Polymer 27:1441
18. Maegawa T, Akashi A, Yaguchi K, Iwasaki Y, Shigetsura YM, Sajiki H (2009) Chem Eur J
15:6953
19. Olberg RC, Pines H, Ipatieff VN (1943) J Am Chem Soc 65:2260
20. Pines H, Kobynski TP (1970) J Catal 17:394
182
A.J. Moreno-Vargas and P. Vogel