Iterative asymmetric synthesis of protected anti-1,3-polyols

Tetrahedron Letters

Volumn 40, Issue 22, 1999, Pages 4169-4172

  Enders, Dieter ^a   Hundertmark, Thomas ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Alkylation; Asymmetric synthesis; Hydrazones; Iteration

Indexed keywords

1,3 DIOXANE DERIVATIVE; DIOXANE; FUNCTIONAL GROUP; HYDRAZONE DERIVATIVE; IODIDE; POLYOL;

ALKYLATION; ARTICLE; DIASTEREOISOMER; ENANTIOMER; SYNTHESIS;

EID: 0033612165     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00645-0     Document Type: Article

References (13)

1. Omura, S.; Tanaka, H. In Macrolide Antibiotics: Chemistry, Biology and Practice; Omura, S., Ed.; Academic Press: New York, 1984; p. 351.
2. For leading references see: (a) Schneider, C. Angew. Chem. 1998, 110, 1445;
3. Angew. Chem., Int. Ed. 1998, 37, 1375;
4. (b) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021.
5. Weigand, S.; Brückner, R. Liebigs Ann./Receueil 1997, 1657 and references cited therein.
6. Enders, D.; Hundertmark, T.; Lampe, C.; Jegelka, U.; Scharfbillig, I. Eur. J. Org. Chem. 1998, 2839.
7. Enders, D.; Hundertmark, T.; Lazny, R. Synlett 1998, 721.
8. Barton, D. H. R.; McCombie, S. W. J. J. Chem. Soc., Perkin Trans. 1 1975, 1574.
9. Hwu, J. R.; Chua, V.; Schroeder, J. E.; Barans, R. E.; Khoudary, K. P.; Wang, N.; Wetzel, J. M. J. Org. Chem. 1986, 51, 4733.
10. Corey, E. J.; Pyne, S. G.; Su, W. Tetrahedron Lett. 1983, 24, 4883.
11. Mori, K.; Watanabe, H.; Yanagi, K.; Minobe, M. Tetrahedron 1985, 41, 3663.
12. The addition of sodium bicarbonate is essential to prevent decomposition of the acetonide.
13. 7 (582.77); calcd: C, 72.13; H, 8.65; found: C, 71.99; H, 8.83.