Efficient and convenient pyridine ring-e formation of the cytotoxic marine alkaloid ascididemin and related analogues

Synthetic Communications

Volumn 27, Issue 15, 1997, Pages 2587-2592

  Lindsay, Brent S ^a   Pearce, A Norrie ^a   Copp, Brent R ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM CHLORIDE; ASCIDIDEMIN; PARAFORMALDEHYDE; PYRIDINE DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; CYTOTOXICITY; DRUG SYNTHESIS; NONHUMAN; REACTION ANALYSIS; STRUCTURE ANALYSIS; THYLAKOID MEMBRANE;

EID: 0030833832     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708004128     Document Type: Article

References (11)

1. Molinski, T.F. Chem. Rev. 1993, 93, 1825.
2. Kobayashi, J., Cheng, J.-F., Nakamura, H., Ohizumi, Y., Hirata, Y., Sasaki, T., Ohta, T., Nozoe, S. Tetrahedron Lett. 1988, 29, 1177.
3. Bonnard, I., Bontemps, N., Lahmy, S., Banaigs, B., Combaut, G., Francisco, C., Colson, P., Houssier, C., Waring, M.J., Bailly, C. Anticancer Drug Design 1995, 10, 333.
4. Lindsay, B.S., Barrows, L.R., Copp, B.R. Bio. Med. Chem. Lett. 1995, 5, 739.
5. Bracher, F. Heterocycles 1989, 29, 2093.
6. Peterson, J.R., Zjawiony, J.K., Liu, S., Hufford, C.D., Clark, A.M., Rogers, R.D. J. Med. Chem. 1992, 35, 4069.
7. Carroll, A.R., Scheuer, P.J. J. Org. Chem. 1990, 55, 4426.
8. Kitahara, Y., Nakahara, S., Yonezawa, T., Nagatsu, M., Kubo, A. Heterocycles 1993, 36, 943.
9. 4 Repeated testing on freshly prepared material has shown the correct value to be 74 μM.
10. Gunawardana, G.P., Kohmoto, S., Gunasekera, S.P., McConnell, O.J., Koehn, F.E. J. Am. Chem. Soc. 1988, 110, 4856.
11. 6 with TMS, 100 MHz), δ 116.54 (obscured, C-12c), 117.23 (dd, J = 167, 9, C-3), 123.01 (m, C-3b), 124.03 (ddd, J = 163, 7, 2, C-4), 130.97 (dd, J = 163, 8, C-5), 131.93 (dd, J = 163, 6, C-6), 131.98 (dd, J = 163, 8, C-7), 136.03 (d, J = 2.4, C-9a), 137.16 (m, C-3a), 144.83 (ddd, J = 8, 8, 2, C-7a), 147.06 (d, J = 11.2, C-12b), 147.20 (s, C-8a), 148.98 (dd, J = 181, 4, C-2), 157.79 (d, J = 14.4, C-12a), 162.69 (d, J =217, C-11), 176.12 (s, C-9).