The enantioselective total synthesis of a β-carboline alkaloid, (S)-(-)-dichotomine C

Chemical and Pharmaceutical Bulletin

Volumn 56, Issue 2, 2008, Pages 237-238

  Omura, Kana ^a   Choshi, Tominari ^a   Watanabe, Shiroh ^a   Satoh, Yuhsuke ^a   Nobuhiro, Junko ^a   Hibino, Satoshi ^a  

^a FUKUYAMA UNIVERSITY   (Japan)

Author keywords

(S) ( ) dichotomine C; Aza electrocyclic reaction; Enantioselective synthesis; First synthesis; Microwave

Indexed keywords

1 AZAHEXATRIENE; ALKALOID DERIVATIVE; ANTIALLERGIC AGENT; BETA CARBOLINE; DICHOTOMINE C; HETEROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; DIHYDROXYLATION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; MICROWAVE RADIATION; SHARPLESS EPOXIDATION;

ANTI-ALLERGIC AGENTS; CARBOLINES; CHEMISTRY, PHYSICAL; CYCLIZATION; HYDROXYLATION; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MICROWAVES; STEREOISOMERISM;

EID: 38849103831     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.56.237     Document Type: Article

References (15)

1. Sun B., Morikawa T., Matsuda H., Tewtrakul S., Wu L. J., Harima S., Yoshikawa M., J. Nat. Prod., 67, 1464-1469, (2004).
2. Woodward R. B., Hoffmann R., "The Conservation of Orbital Symmetry," Chap. 5, Verlag Chemie, Weinheim, 1970.
3. Marvel E. N., "Thermal Electrocyclic Reactions," Chap. 2, Academic Press, New York, 1980.
4. Okamura W. H., de Lera A. R., "Comprehensive Organic Synthesis," Vol. 5, ed. by Trost B. M., Fleming I., Paquette L. A., Pergamon Press, New York, 1991, pp. 699-750.
5. Hibino S., Sugino E., "Advances in Nitrogen Heterocycles," Vol. 5, ed. by Moody C. J., JAI Press, Greenwich, CT, 1995, pp. 699-750.
6. Choshi T., Yakugaku Zasshi, 121, 487-495 (2001).
7. Choshi T., Uchida Y., Kubota Y., Nobuhiro J., Takeshita M., Hatano T., Hibino S., Chem. Pharm. Bull., 55, 1060-1064 (2007) and related references cited therein.
8. Kumemura T., Choshi T., Yukawa J., Hirose A., Nobuhiro J., Hibino S., Heterocycles, 66, 87-90 (2005) and related references cited therein.
9. Choshi T., Sada T., Fujimoto H., Nagayama C., Sugino E., Hibino S., J. Org. Chem., 62, 2535-2543 (1997).
10. Heck R. F., Org. Reactions, 27, 345 (1982).
11. Yan H., Kerns J. K., Jin Q., Zhu C., Barnette M. S., Callahan J. F., Hay D. W. P., Jolivette L. J., Synth. Commun., 35, 3105-3112 (2005).
12. Kuwada T., Fukui M., Hirayama M., Nobuhiro J., Choshi T., Hibino S., Heterocycles, 58, 325-332 (2002).
13. 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., 57, 2768-2771 (1992).
14. 1H-NMR ratio of their (R)-MαNP esters, which was synthesized by esterification of the C15-primary hydroxy group in dichotomine C (1) with pivaloyl chloride, followed by treatment of the C14-secondary hydroxy group with (R)-2-methoxy-2-(1-naphthyl)propionic acid (MαNP acid) in the presence of dicyclohexylcarbodiimide and dimethylaminopyridine.
15. 6 by the corrected information from Professor M. Yoshikawa.