Diastereoselective Titanium Enolate Aldol Reaction for the Total Synthesis of Epothilones

Organic Letters

Volumn 4, Issue 22, 2002, Pages 3811-3814

  Koch, Guido ^a   Loiseleur, Olivier ^a   Fuentes, Daniel ^a   Jantsch, Andrea ^a   Altmann, Karl Heinz ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ANTINEOPLASTIC AGENT; EPOTHILONE B; EPOTHILONE DERIVATIVE; TITANIUM;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; ANTINEOPLASTIC AGENTS; EPOTHILONES; STEREOISOMERISM; TITANIUM;

EID: 0037600607     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026480b     Document Type: Article

References (14)

1. (a) Mulzer, J.; Mantoulidis, A. Tetrahedron Lett. 1996, 37, 9179.
2. (b) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang. Z. Angew. Chem., Int. Ed. Engl. 1997, 36, 166.
3. (a) Nicolaou, K. C.; Roschangar, F.; Vourloumis, D. Angew. Chem., Int. Ed. 1998, 37, 2014.
4. (b) Schinzer, D.; Bauer, A.; Böhm, O. M.; Limberg, A.; Cordes, M. Chem.-Eur. J. 1999, 5, 2483.
5. (c) Schinzer, D.; Bauer, A.; Schieber, J. Chem.-Eur. J. 1999, 5, 2492.
6. (d) Balog, A.; Harris, C.; Savin, K.; Zhang, X. G.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. 1998, 37, 2675.
7. (e) Harris, C. R.; Kuduk, S. D.; Balog, A.; Savin, K.; Glunz, P. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 7050.
8. (f) Wu, Z.; Zhang, F.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2000, 39, 4505.
9. (g) Mulzer, J.; Mantoulidis, A.; Öhler, E. J. Org. Chem. 2000, 65, 7456.
10. (a) Preparation of the aldehyde 2: Nicolaou, K. C.; Ninkovic, S.; Sarabia, F.; Vourloumis, D.; He, Y.; Vallberg, M. R.; Finlay, M. R. V.; Yang, Z. J. Am. Chem. Soc. 1997, 119, 7974.
11. (b) Preparation of the ketone 1: Altmann, K.-H.; Bold, G.; Caravatti, G.; Denni, D.; Florsheimer, A.; Schmidt, A.; Rhis, G.; Wartmann, M. Helv. Chim. Acta 2002, 85, in press.
12. For the elucidation of the configuration of 6, vide infra.
13. 4 followed by trimethyl silyl enol ether 9a at 0 °C resulted in the decomposition of the aldehyde with no formation of aldol product.
14. The sample 17 derived from the aldol product 3 was identical with the corresponding compound described in the literature (refs 2g and 3a) with respect to all reported properties.