Enantioselective total synthesis of anti HIV-1 active (+)-calanolide A through a quinine-catalyzed asymmetric intramolecular oxo-Michael addition
T Tanaka, T Kumamoto, T Ishikawa
Index: Tanaka, Tomohiro; Kumamoto, Takuya; Ishikawa, Tsutomu Tetrahedron Letters, 2000 , vol. 41, # 52 p. 10229 - 10232
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Citation Number: 42
Abstract
(+)-Calanolide A (1), isolated as a strong anti HIV-1 active coumarin from Calophyllum lanigerum var. austrocoriaceum (Guttiferae), 1 is presently being examined as a possible candidate for an AIDS drug at the clinical level in USA. 2 The (10R,11S,12S) stereochemistry of the 2,3-dimethyl-4-chromanol skeleton (the ring D) in 1 is suggested to be the most responsible function for anti HIV-1 activity. 1. and 3. We have approached the enantioselective construction of ...
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[Flavin, Michael T.; Rizzo, John D.; Khilevich, Albert; Kucherenko, Alla; Sheinkman, Abram K.; Vilaychack, Vilayphone; Lin, Lin; Chen, Wei; Greenwood, Eugenia Mata; Pengsuparp, Thitima; Pezzuto, John M.; Hughes, Stephen H.; Flavin, Thomas M.; Cibulski, Michael; Boulanger, William A.; Shone, Robert L.; Xu, Ze-Qi Journal of Medicinal Chemistry, 1996 , vol. 39, # 6 p. 1303 - 1313]
[Flavin, Michael T.; Rizzo, John D.; Khilevich, Albert; Kucherenko, Alla; Sheinkman, Abram K.; Vilaychack, Vilayphone; Lin, Lin; Chen, Wei; Greenwood, Eugenia Mata; Pengsuparp, Thitima; Pezzuto, John M.; Hughes, Stephen H.; Flavin, Thomas M.; Cibulski, Michael; Boulanger, William A.; Shone, Robert L.; Xu, Ze-Qi Journal of Medicinal Chemistry, 1996 , vol. 39, # 6 p. 1303 - 1313]
[Flavin, Michael T.; Rizzo, John D.; Khilevich, Albert; Kucherenko, Alla; Sheinkman, Abram K.; Vilaychack, Vilayphone; Lin, Lin; Chen, Wei; Greenwood, Eugenia Mata; Pengsuparp, Thitima; Pezzuto, John M.; Hughes, Stephen H.; Flavin, Thomas M.; Cibulski, Michael; Boulanger, William A.; Shone, Robert L.; Xu, Ze-Qi Journal of Medicinal Chemistry, 1996 , vol. 39, # 6 p. 1303 - 1313]