142632-32-4

Basic information

• Product Name: CALANOLIDE A
• Synonyms: CALANOLIDE A;(+)-(10R,11S,12S)-12-HYDROXY-6,6,10,11-TETRAMETHYL-4-PROPYL-11,12-DIHYDRO-2H,6H,10H-BENZO(1,2-B:3,4-B':5,6-B'']TRIPYRAN-2-ONE;CALANOLIDE A,(+)-(10R,11S，12S)-12-HYDROXY-6,6,10,11-TETRAMETHYL-4-PROPYL-11，12-DIHYDRO-2H，6H,10H-BENZO(1，2-B：3,4-B'：5,6-B ]TRIPYRAN-2-ONE;(10R,11S,12S)-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-2-one
• CAS NO: 142632-32-4
• Molecular Formula: C22H26O5
• Molecular Weight: 370.44
• Mol File: 142632-32-4.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 514.8°Cat760mmHg
• Flash Point: 177.2°C
• Appearance: /
• Density: 1.181g/cm³
• Vapor Pressure: 2E-11mmHg at 25°C
• Refractive Index: 1.558
• CAS DataBase Reference: CALANOLIDE A(CAS DataBase Reference)
• NIST Chemistry Reference: CALANOLIDE A(142632-32-4)
• EPA Substance Registry System: CALANOLIDE A(142632-32-4)

Safety Data

• Hazardous Substances Data: 142632-32-4(Hazardous Substances Data)

Usage

Uses

(+)-Calanolide A is an experimental non-nucleoside reverse transcriptase inhibitor. It has potent anti-HIV activity.

InChI:InChI=1/C22H26O5/c1-6-7-13-10-15(23)26-21-16(13)20-14(8-9-22(4,5)27-20)19-17(21)18(24)11(2)12(3)25-19/h8-12,18,24H,6-7H2,1-5H3/t11?,12-,18+/m1/s1

Upstream product

• 107-86-8 3,3-dimethyl acrylaldehyde 
• 685844-44-4 5-hydroxy-8,9-dimethyl-4-propyl-8,9-dihydro-pyrano[2,3-f]chromene-2,10-dione 
• 862805-48-9 C₃₄H₄₆O₇ 
• 166983-58-0 5,7-Dihydroxy-8-propanoyl-4-propyl-2H-1-benzopyran-2-one 
• 3249-68-1 ethyl butyroyl acetate 
• 66346-59-6 5,7-dihydroxy-4-propylcoumarin 
• 31525-67-4 dimethylacetal of 3-methyl-3-hydroxybutyraldehyde 
• 108-73-6 3,5-dihydroxyphenol 
• 263351-94-6 (10R,11S)-10,11-dihydro-4-propyl-6,6,10,11-tetramethyl-2H,6H,12H-benzo[1,2-b;3,4-b';5,6-b'']tripyran-2,12-dione 
• 334881-61-7 (8R,9S)-8,9-dihydro-8,9-dimethyl-5-methoxy-4-propyl-2H,10H-benzo[1,2-b;5,6-b']dipyran-2,10-dione 
• 183904-55-4 HI-D₈₆ 
• 161753-49-7 (+/-)-12-oxocalanolide A 
• 166983-61-5 HI-D₁₂ 
• 185339-28-0 5-Hydroxy-6-((2R,3R)-3-hydroxy-2-methyl-butyryl)-2,2-dimethyl-10-propyl-2H-pyrano[2,3-f]chromen-8-one 

Relevant articles and documents

Synthesis of Optically Active Calanolides A and B

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Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (±)-calanolide A and its enantiomers

The anti-HIV agent (±)-calanolide A (1) has been synthesized in a five- step approach starting with phloroglucinol [→ 5 → 6 → 11 → 18 → (±)- 1], which includes Pechmann reaction, Friedel-Crafts acylation, chromenylation with 4,4-dimethoxy-2-methylbutan-2-ol, cyclization, and Luche reduction. Cyclization of chromene 11 to chromanone 18 was achieved by employing either acetaldehyde diethyl acetal or paraldehyde in the presence of trifluoroacetic acid and pyridine or PPTS. Luche reduction of chromanone 18 at lower temperature preferably yielded (±)-1. Reduction of chromone 12, synthesized by Kostanecki-Robinson reaction from chromene 11, failed to afford (±)-1. The synthetic (±)-1 has been chromatographically resolved into its optically active forms, (+)- and (-)-1. The anti-HIV activities for synthetic (±)-1, as well as resultant (+)- and (-)-1, have been determined. Only (+)-1 accounted for anti-HIV activity, which was similar to the data reported for the natural product, and (-)-1 was inactive.

Concise Synthesis of Anti-HIV-1 Active (+)-Inophyllum B and (+)-Calanolide A by Application of (-)-Quinine-Catalyzed Intramolecular Oxo-Michael Addition

(-)-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

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.