Complex aldol reactions for the construction of dense polyol stereoarrays: Synthesis of the C33-C36 region of aflastatin A

Organic Letters

Volumn 7, Issue 15, 2005, Pages 3331-3333

  Evans, David A ^a   Glorius, Frank ^a   Burch, Jason D ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; AFLASTATIN A; BORON DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; STREPTOMYCES; SYNTHESIS;

BORON COMPOUNDS; MOLECULAR STRUCTURE; PYRROLIDINONES; STEREOISOMERISM; STREPTOMYCES;

EID: 23044470281     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051226f     Document Type: Article

References (14)

1. Sakuda, S.; Ono, M.; Furihata, K.; Nakayama, J.; Suzuki, A.; Isogai, A. J. Am. Chem. Soc. 1996, 118, 7855.
2. Ikeda, H.; Matsumori, N.; Ono, M.; Suzuki, A.; Isogai, A.; Nagasawa, H.; Sakuda, S. J. Org. Chem. 2000, 65, 438.
3. Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920.
4. See Supporting Information for details of the synthesis of 2.
5. Goodman, J. M.; Paterson, I. Tetrahedron Lett. 1992, 33, 7233.
6. Marco, J. A.; Carda, M.; Falomir, E.; Palomo, C.; Oiarbide, M.; Ortiz, J. A.; Linden, A. Tetrahedron Lett. 1999, 40, 1065.
7. Galobardes, M.; Gascón, M.; Mena, M.; Romea, P.; Urpí, F.; Vilarassa, J. Org. Lett. 2000, 2, 2599.
8. Adduct 4 was formed as a single diastereomer, consistent with the formation of the (Z) enolate, which is expected for α′-siloxy ketones: Murga, J.; Falomir, E.; Carda, M.; Gonzalez, F.; Marco, J. A. Org. Lett. 2001, 3, 901.
9. See Supporting Information for experiments that support all stereochemical assignments.
10. Evans, D. A.; Nelson, J. V.; Vogel, E.; Taber, T. R. J. Am. Chem. Soc. 1981, 103, 3099.
11. Similarly, it has been noted that (E) crotylboronates react faster with aldehydes than the corresponding (Z) isomers: Roush, W. R.; Adam, M. A.; Walts, A. E.; Harris, D. J. J. Am. Chem. Soc. 1986, 108, 3422.
12. Evans, D. A.; Gage, J. R.; Leighton, J. L.; Kim, A. S. J. Org. Chem. 1992, 1961.
13. In no case were products derived from α′-enolization observed.
14. The syntheses of compounds 10 and 11 will be reported in due course.