161753-49-7Relevant academic research and scientific papers
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.
Total Synthesis of (+/-)-Calanolide A, a Non-Nucleoside Inhibitor of HIV-1 Reverse Transcriptase
Chenera, Balan,West, Michael L.,Finkelstein, Joseph A.,Dreyer, Geoffrey B.
, p. 5605 - 5606 (1993)
The first syntheses of (+/-)-calanolide A and the related (+/-)-calanolides C and D have been carried out in a short sequence using a Lewis acid-promoted Claisen rearrangement to establish the chromene ring.
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.
A versatile approach for synthesis of 2,3-dimethyl chroman-4-ones, intermediate for calanolide anti-HIV agents, via aldol/Mitsunobu reactions
Khilevich, Albert,Rizzo, John D.,Flavin, Michael T.,Sheinkman, Abram K.,Mar, Aye,Kucherenko, Alla,Yan, Changren,Dzekhtser, Sergey,Brankovic, Darko,Lin, Lin,Liu, Jinjun,Rizzo, Thomas M.,Xu, Ze-Qi
, p. 3757 - 3771 (1996)
Combined aldol/Mitsunobu reactions have been employed for the first time for synthesis of 2,3-dimethyl chroman-4-ones, intermediates for calanolide anti-HIV agents. Thus, the lithium enolate of chromene 1 reacted with acetaldehyde at -78°C to afford the aldol products 4 and 5. Under Mitsunobu conditions (Ph3P/DEAD), the syn aldol product 4 led to the formation of trans-2,3-dimethyl chroman-4-one 2 while the anti aldol product 5 yielded both trans and cis derivative (2 and 3). The use of other phosphorous and azo compounds in this reaction has also been investigated.
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
Preparation of a trans-calanolide ketone intermediate and chiral separation of calanolide alcohols to give racemic calanolide A
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Page column 17, (2010/02/08)
The method of the invention comprises a process for synthesizing a trans-calanolide A ketone intermediate used in the synthesis of racemic trans-calanolide A. The invention further comprises a method for removing a racemic calanolide B diastereomer from a
PROCESSES FOR PREPARING CALANOLIDE A AND INTERMEDIATES THEREOF
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Page/Page column 20, (2008/06/13)
The present invention provides a production method of Calanolide A according to the following method wherein each symbol is as defined in the specification, as a more convenient and industrially practical method for the synthesis of Calanolide A from an easily available starting material.
Methods for preparing antiviral calanolide compounds
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, (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.
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.
