Chemoselectivity in the manipulation of polyhydroxylated compounds derived from the diastereoselective dihydroxylation of optically active allylic enoate alcohols

Tetrahedron

Volumn 52, Issue 23, 1996, Pages 7861-7874

  Barros, M Teresa ^a,c   Januario Charmier, M Odile ^a   Maycock, Christopher D ^a,b   Pires, Mariana ^a  

^a INSTITUTO DE TECNOLOGIA QUÍMICA E BIOLÓGICA   (Portugal)

^b UNIVERSITY OF LISBON   (Portugal)

^c UNIVERSIDADE NOVA DE LISBOA   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALLYL COMPOUND; LACTONE; POLYOXIN D; SWAINSONINE; URACIL; ZARAGOZIC ACID A;

ARTICLE; DRUG ACTIVITY; DRUG SYNTHESIS; HYDROXYLATION; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; STEM CELL; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0030070161     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00357-2     Document Type: Article

References (30)

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19. Cha, J.K.; Christ, W.J.; Kishi, Y., Tetrahedron. 1984, 40, 2247. Houk, K.N.; Duh, H-Y.; Wu, Y-D.; Moses, S.R., J. Am. Chem. Soc., 1986, 108, 2754. Vedejs, E.; Dent, W.H. III, J. Am. Chem. Soc., 1989, 111, 6861. Evans, D.A.; Kaldor, S.W., J. Org. Chem., 1990, 55, 1698. Hale, K.J.; Manaviazar, S.; Peak, S.A. Tetrahedron Lett. 1994, 35, 425. Kolb, H.C.; VanNieuwenhze, M.S.; Sharpless, K.B. Chem. Rev. 1994, 94, 2483.
20. Cha, J.K.; Christ, W.J.; Kishi, Y., Tetrahedron. 1984, 40, 2247. Houk, K.N.; Duh, H-Y.; Wu, Y-D.; Moses, S.R., J. Am. Chem. Soc., 1986, 108, 2754. Vedejs, E.; Dent, W.H. III, J. Am. Chem. Soc., 1989, 111, 6861. Evans, D.A.; Kaldor, S.W., J. Org. Chem., 1990, 55, 1698. Hale, K.J.; Manaviazar, S.; Peak, S.A. Tetrahedron Lett. 1994, 35, 425. Kolb, H.C.; VanNieuwenhze, M.S.; Sharpless, K.B. Chem. Rev. 1994, 94, 2483.
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22. From D-Mannitol and D-tartaric acid by multistep processes.
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28. Selective reactions at the α-hydroxyl are possible and we have been able to produce cyclic carbonates which prevent lactonisation.
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30. 2-symmetric diol diendioate 6 is prepared from inexpensive D-mannitol by a lengthy process. This causes a bottleneck but we are working on a method of preparing this compound by a simpler route having less steps, from symmetric starting materials.