Molecular diversity of tonghaosu: Synthesis of lactam-containing tonghaosu analogs

Synthesis

Volumn , Issue 13, 2003, Pages 1995-2000

  Yin, Biao Lin ^a   Yang, Zheng Min ^a   Hu, Tai Shan ^a   Wu, Yu Lin ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Antifeedant; Diastereoselective; Lactam; Spiroketalization; Tonghaosu analogs

Indexed keywords

ALCOHOLS; AMINO ACIDS; STEREOCHEMISTRY;

CHIRALITY;

SYNTHESIS (CHEMICAL);

2 (2,4 HEXADIYNYLIDENE) 1,6 DIOXASPIRO[4.4]NON 3 ENE; ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; LACTAM; METHYL 2 FUROATE; METHYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; IONIZING RADIATION; MOLECULAR DYNAMICS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0141506891     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41042     Document Type: Article

References (20)

1. Partial result has been published: Wu, Z.-H.; Wang, J.; Li, J.-C.; Xu, Y.-Z.; Yu, A.-L.; Feng, Z.-R.; Shen, J.; Wu, Y.-L.; Guo, P.-F.; Wang, Y.-N. Nat. Prod. R & D [China] 1994, 6, 1; Chem. Abstr. 121, 101920.
2. Partial result has been published: Wu, Z.-H.; Wang, J.; Li, J.-C.; Xu, Y.-Z.; Yu, A.-L.; Feng, Z.-R.; Shen, J.; Wu, Y.-L.; Guo, P.-F.; Wang, Y.-N. Nat. Prod. R & D [China] 1994, 6, 1; Chem. Abstr. 121, 101920.
3. (a) Hegnauer, R. In Chemotaxonomie der Pflanzen, Vol. 3; Birkhauser Verlag: Basel, 1964, 447.
4. (b) Bohlmann, F.; Burkhardt, T.; Zdero, C. Naturally Occurring Acetylenes; Academic Press: London, 1973.
5. (c) Greger, H. In The Biology and Chemistry of Compositae; Heywood, V. H.; Harborne, J. B.; Turner, B. L., Eds.; Academic Press: London, 1977, Chap. 32.
6. (d) Bohlmann, F. In Chemistry and Biology of Naturally Occurring Acetylenes and Related Compounds; Lam, J.; Bretler, H.; Anason, T.; Hansen, L., Eds.; Elsvier: Amsterdam, 1988, 1.
7. (e) Zdero, C.; Bohlmann, F. Plant Syst. Evol. 1990, 171, 1.
8. (a) Bohlmann, F.; Jastrow, H.; Ertringshausen, G.; Kramer, D. Chem. Ber. 1964, 97, 801.
9. (b) Bohlmann, F.; Florentz, G. Chem. Ber. 1966, 99, 990.
10. (a) Gao, Y.; Wu, W.-L.; Ye, B.; Zhou, R.; Wu, Y.-L. Tetrahedron Lett. 1996, 37, 893.
11. (b) Gao, Y.; Wu, W.-L.; Wu, Y.-L.; Ye, B.; Zhou, R. Tetrahedron 1998, 54, 12523.
12. (a) Fan, J.-F.; Zhang, Y.-F.; Wu, Y.; Wu, Y.-L. Chinese J. Chem. 2001, 19, 1254; Chem. Abstr. 136, 263012.
13. (a) Fan, J.-F.; Zhang, Y.-F.; Wu, Y.; Wu, Y.-L. Chinese J. Chem. 2001, 19, 1254; Chem. Abstr. 136, 263012.
14. (b) Fan, J.-F.; Yin, B.-L.; Zhang, Y.-F.; Wu, Y.-L.; Wu, Y. Huaxue Xuebao 2001, 59, 1756; Chem. Abstr. 136, 083647.
15. (b) Fan, J.-F.; Yin, B.-L.; Zhang, Y.-F.; Wu, Y.-L.; Wu, Y. Huaxue Xuebao 2001, 59, 1756; Chem. Abstr. 136, 083647.
16. Blanchette, J. A.; Brown, E. V. J. Am. Chem. Soc. 1952, 74, 2098.
17. Fan, J.-F. Ph. D. Thesis; Shanghai Institute of Organic Chemistry: China, 2000.
18. Yin, B.-L.; Fan, J.-F.; Gao, Y.; Wu, Y.-L. Synlett 2003, 399.
19. Reviews: (a) Brimble, M. A.; Fares, F. A. Tetrahedron 1999, 55, 7661. (b) Mead, K. T.; Brewer, B. N. Curr. Org. Chem. 2003, 7, 227; and references cited therein.
20. Reviews: (a) Brimble, M. A.; Fares, F. A. Tetrahedron 1999, 55, 7661. (b) Mead, K. T.; Brewer, B. N. Curr. Org. Chem. 2003, 7, 227; and references cited therein.