Asymmetric total synthesis of the proposed structure of the medicinal alkaloid jamtine using the chiral base approach

Organic Letters

Volumn 5, Issue 4, 2003, Pages 535-537

  Simpkins, Nigel S ^a   Gill, Christopher D ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; ALKALOID JAMTINE; AMIDE; BASE; IMIDE; NATURAL PRODUCT; PLANT EXTRACT; UNCLASSIFIED DRUG; ALKALOID; AMINE; ISOQUINOLINE DERIVATIVE; JAMTINE; LITHIUM;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL REACTION; CHIRALITY; DESYMMETRIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; MEDICINAL PLANT; CHEMISTRY; PAKISTAN; STEREOISOMERISM; SYNTHESIS; TRADITIONAL MEDICINE;

ALKALOIDS; AMINES; IMIDES; ISOQUINOLINES; LITHIUM; MEDICINE, TRADITIONAL; PAKISTAN; PLANTS, MEDICINAL; STEREOISOMERISM;

EID: 0037669296     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027447s     Document Type: Article

References (13)

1. Adams, D. J.; Blake, A. J.; Cooke, P. A.; Gill, C. D.; Simpkins, N. S. Tetrahedron 2002, 58, 4603 (part of a special issue dedicated to chiral lithium amides).
2. For a review, see: O'Brien, P. J. Chem. Soc., Perkin Trans. 1 1998, 1439.
3. Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
4. Padwa, A.; Danca, M. D. Org. Lett. 2002, 4, 715.
5. Ahmad, V. U.; Rahman, A.; Rasheed, T.; Rehman, H. Heterocycles 1987, 26, 1987. See also: Rasheed, T.; Khan, M. N. I.; Zhadi, S. S. A.; Durrani, S. J. Nat. Prod. 1991, 54, 582. Ahmad, V. U.; Iqbal, S. Nat. Prod. Lett. 1993, 2, 105.
6. Ahmad, V. U.; Rahman, A.; Rasheed, T.; Rehman, H. Heterocycles 1987, 26, 1987. See also: Rasheed, T.; Khan, M. N. I.; Zhadi, S. S. A.; Durrani, S. J. Nat. Prod. 1991, 54, 582. Ahmad, V. U.; Iqbal, S. Nat. Prod. Lett. 1993, 2, 105.
7. Ahmad, V. U.; Rahman, A.; Rasheed, T.; Rehman, H. Heterocycles 1987, 26, 1987. See also: Rasheed, T.; Khan, M. N. I.; Zhadi, S. S. A.; Durrani, S. J. Nat. Prod. 1991, 54, 582. Ahmad, V. U.; Iqbal, S. Nat. Prod. Lett. 1993, 2, 105.
8. Chopra, R. N.; Chopra, I. C.; Handa, K. L.; Kapoor, L. D. Indigenous Drugs of India; U. N. Dhar and Sons Pvt. Ltd.; Calcutta, India, 1958.
9. Base 11, in either mono- or dilithiated form always gives enantiocomplementary results to base 3. At present our assignment of absolute stereochemistry for 10 rests on this fact, along with a firmly established pattern of enantioselectivity for base 3 (see ref 1).
10. For related examples of regioselective imide reduction, see: Pilli, R. A.; Russowsky, J. Org. Chem. 1996, 61, 3187. Hsu, R.-T.; Cheng, L.-M.; Chang, N.-C.; Tai, H.-M. J. Org. Chem. 2002, 67, 5044.
11. For related examples of regioselective imide reduction, see: Pilli, R. A.; Russowsky, J. Org. Chem. 1996, 61, 3187. Hsu, R.-T.; Cheng, L.-M.; Chang, N.-C.; Tai, H.-M. J. Org. Chem. 2002, 67, 5044.
12. Martin, S. F.; Clark, C. W.; Ito, M.; Mortimore, M. J. Am. Chem. Soc. 1996, 118, 9805.
13. 1H NMR spectra obtained by us for compounds 13, 5, and 14 are virtually identical with those kindly forwarded to us by Prof. Padwa. In a personal communication Prof. Padwa has also indicated that the structure of "jamtine" 5 has been secured by X-ray crystallography. A full report by this group, in which they reach similar conclusions to ours, has been recently published; see: Padwa, A.; Danca, M. D.; Hardcastle, K. I.; McClure, M. S. J. Org. Chem. 2003, 68, 929.