Synthesis of stereodefined z-vinyl iodides from carbohydrates as a prelude to C/D ring assembly in taxanes

Tetrahedron Letters

Volumn 40, Issue 18, 1999, Pages 3519-3522

  Paquette, Leo A ^a   Shih, Tzenge Lien ^a   Zeng, Qingbei ^a   Hofferberth, John E ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

Alkenyl halides; Carbohydrates; Oxetanes; Wittig reactions

Indexed keywords

CARBOHYDRATE; TAXANE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033617268     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00546-8     Document Type: Article

References (10)

1. (1) (a) Paquette, L. A.; Zhao, M. J. Am. Chem. Soc. 1998, 120, 5203.
2. (b) Paquette, L. A.; Wang, H.-L.; Su, Z.; Zhao, M. J. Am. Chem. Soc. 1998, 120, 5213.
3. (2) For a recently reported use of this substance, consult Paquette, L. A.; Wang, H.-L.; Zeng, Q.; Shih, T. L. J. Org. Chem. 1998, 63, 6432.
4. (3) (a) Paquette, L. A.; Montgomery, F. J.; Wang, T.-Z. J. Org. Chem. 1995, 60, 7857.
5. (b) Paquette, L. A.; Zeng, Q.; Tsui, H.-C.; Johnston, J. N. J. Org. Chem. 1998, 63, 8491.
6. (4) Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 2173.
7. (5) Stork, G.; Manabe, K.; Liu, L. J. Am. Chem. Soc. 1998, 120, 1337.
8. (6) Tsui, H.-C.; Paquette, L. A. J. Org. Chem. 1998, 63, 9968.
9. (7) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
10. 13C NMR, and MS spectra/combustion data in satisfactory agreement with the assigned structures.