Enantiocontrolled synthesis of (+)-boronolide

Journal of Organic Chemistry

Volumn 61, Issue 15, 1996, Pages 4944-4948

  Honda, Toshio ^a   Horiuchi, Satomi ^a   Mizutani, Hirotake ^a   Kanai, Kazuo ^a  

^a HOSHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BORONOLIDE; POLYOL; UNCLASSIFIED DRUG;

ARTICLE; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030018221     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960267+     Document Type: Article

References (15)

1. Franca, N. C.; Polonsky, J. C. R. Hebd. Séances, Acad. Sci., Ser. C 1971, 273, 439.
2. Davies-Coleman, M. T.; Rivett, D. E. A. Phytochemistry 1987, 26, 3047.
3. Watt, J. M.; Brandwijk, M. G. B. The Medicinal and Poisonous Plants of Southern and Eastern Africa; Livingstone: Edinburgh, 1962; p 516.
4. Kjaer, A.; Norrestam, R.; Polonsky, J. Acta. Chem. Scand., Ser. B 1985, 39, 745.
5. Jefford, C. W.; Moulin, M.-C. Helv. Chim. Acta 1991, 74, 336.
6. Nagano, H.; Yasui, H. Chem. Lett. 1992, 1045.
7. (a) Sharpless, K. B.; Amberg, W.; Beller, M.; Chen, H.; Hartung, J.; Kawanami, Y.; Lübben, D.; Manoury, E.; Ogino, Y.; Shibata, T.; Ukita, T. J. Org. Chem. 1991, 56, 4585.
8. (b) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
9. (c) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483 and references cited therein.
10. (a) Jeong, K.-S.; Sjö, P.; Sharpless, K. B. Tetrahedron Lett. 1992, 33, 3833.
11. (b) Tani, K.; Sato, Y.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1993, 34, 4975.
12. Brown, H. C.; Hamaoka, T; Ravindran, N. J. Am. Chem. Soc. 1973, 95, 5786.
13. The ee was determined by HPLC analysis of the bis-benzoyl ester of 6 using a Chiralcel OD column (Daicel Chemical Industries, LTD.).
14. Cha, J. K.; Kim, N.-S. Chem. Rev. 1995, 95, 1761.
15. Wang, L.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7568.