161753-49-7Relevant articles and documents
Total synthesis of (±)-Calanolide A
Rehder, Ken S.,Kepler, John A.
, p. 4005 - 4021 (1996)
The total synthesis of (±)-Calanolide A, incorporating a ring-forming sequence different from previous procedures, is described.
Novel Approach for Synthesis of (+/-)-Calanolide A and Its Anti-HIV Activity
Kucherenko, Alla,Flavin, Michael T.,Boulanger, William A.,Khilevich, Albert,Shone, Robert L.,et al.
, p. 5475 - 5478 (1995)
Anti-HIV agent (+/-)-calanolide A (1) has been synthesized.The key intermediate, chromone 5, was synthesized by the sequence of Pechmann reaction, acylation and chromenylation by 4,4-dimethoxy-2-methylbutan-2-ol.The anti-HIV activity for synthetic (+/-)-1 has been determined and compared with the natural product.
Structure-activity modifications of the HIV-1 inhibitors (+)-calanolide A and (-)-calanolide B
Galinis, Deborah L.,Fuller, Richard W.,McKee, Tawnya C.,Cardellina II, John H.,Gulakowski, Robert J.,McMahon, James B.,Boyd, Michael R.
, p. 4507 - 4510 (1996)
The Δ7,8 olefinic linkages within (+)-calanolide A (1) and (-)- calanolide B (2) were catalytically reduced to determine impact on the anti- HIV activity of the parent compounds. In addition, a series of structure modifications of the C-12 hydroxyl group in (-)-calanolide B was made to investigate the importance of that substituent to the HIV-1 inhibitory activity of these coumarins. A total of 14 analogs were isolated or prepared and compared to (+)-calanolide A and (-)-calanolide B in the NCI primary anti-HIV assay. While none of the compounds showed activity superior to the two unmodified leads, some structure-activity requirements were apparent from the relative anti-HIV potencies of the various analogs.
Concise Synthesis of Anti-HIV-1 Active (+)-Inophyllum B and (+)-Calanolide A by Application of (-)-Quinine-Catalyzed Intramolecular Oxo-Michael Addition
Sekino, Etsuko,Kumamoto, Takuya,Tanaka, Tomohiro,Ikeda, Tomoko,Ishikawa, Tsutomu
, p. 2760 - 2767 (2007/10/03)
(-)-Quinine-catalyzed intramolecular oxo-Michael addition (IMA) of 7-hydroxy-5-methoxy-8-tigloylcoumarins was developed for the enantioselective construction of 2,3-dimethyl-4-chromanone systems in the context of the asymmetric synthesis of anti-HIV-1 act
Methods for preparing antiviral calanolide compounds
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Example 22, (2008/06/13)
The present invention relates to methods for preparing 2,2-dimethyl-5-acyloxy-10-propyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-8-one (5) and 2,2-dimethyl-5-hydroxy-10-propyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-8-one (6) and their use as intermediates for the synthesis of antiviral calanolide compounds. For example, Fries rearrangement on compound 5 or Friedel-Crafts reaction on 6, yields intermediate 2,2-dimethyl-5-hydroxy-6-propionyl-10-propyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-8-one (4), which, in turn, can be converted to (+)-calanolide A and (?)-calanolide B. The coupling of compound 6 with the appropriate chiral molecule under Mitsunobu or nucleophilic displacement leads to the asymmetric synthesis of antiviral calanolide compounds.