17312-31-1

Upstream product

• 628-13-7 pyridine hydrochloride 
• 548-27-6 calophyllolide 
• 98192-65-5 5,7-Dihydroxy-8-(2-methylbutanoyl)-4-phenyl-2H-chromen-2-one 
• 685844-48-8 (8R,9S)-5-Hydroxy-8,9-dimethyl-4-phenyl-8,9-dihydro-pyrano[2,3-f]chromene-2,10-dione 
• 680575-77-3 (8R,9S)-8,9-dihydro-8,9-dimethyl-5-methoxy-4-phenyl-2H,10H-benzo[1,2-b;5,6-b']dipyran-2,10-dione 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 685844-45-5 (8R,9R)-5-Hydroxy-8,9-dimethyl-4-phenyl-8,9-dihydro-pyrano[2,3-f]chromene-2,10-dione 
• 41135-07-3 (+)-cis-dihydroinophyllolide 
• 172805-13-9 6-(2-Bromo-2-methylbutanoyl)-5-methoxy-2,2-dimethyl-10-phenyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-8-one 
• 161633-70-1 5-Methoxy-2,2-dimethyl-6-(2-methylbutanoyl)-10-phenyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-8-one 
• 31525-67-4 dimethylacetal of 3-methyl-3-hydroxybutyraldehyde 
• 5302-74-9 mammea A/BB cyclo D 
• 172805-18-4 5-Hydroxy-2,2-dimethyl-6-<(E)-2-methylbut-2-enoyl>-10-phenyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-8-one 

Downstream Products

• 41135-07-3 (+)-cis-dihydroinophyllolide 
• 41135-08-4 NC 127858 
• 41135-08-4 (10R,11S,12R)-12-Hydroxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-6H,10H-dipyrano[2,3-f;2',3'-h]chromen-2-one 
• 41135-08-4 (+/-)-Inophyllum B 
• 477-23-6 (+/-)-3c-(5-hydroxy-2r,3t,8,8-tetramethyl-4-oxo-3,4-dihydro-2H,8H-pyrano[2,3-f]chromen-6-yl)-3t-phenyl-acrylic acid 
• 121968-71-6 (+/-)-3c-(5-methoxy-2r,3t,8,8-tetramethyl-4-oxo-3,4-dihydro-2H,8H-pyrano[2,3-f]chromen-6-yl)-3t-phenyl-acrylic acid methyl ester 

Relevant academic research and scientific papers

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

Synthesis of the Calophyllum coumarins. Part 2

Synthetic routes leading to the synthesis of the natural 4-phenyl, 4-propyl and 4-methyl coumarins isolated from Calophyllum sp. are presented. 4-Aryl or -alkyl, 8- and 6-acyl 5,7-dihydroxy coumarins were chromenylated and then methylated at the 5 or 7 positions.A 4-step hydrobromination-bromination-double dehydrobromination sequence converted the 2-methylbutanoyl side chain into the (E)-2-methylbut-2-enoyl (tigloyl) group to give calophyllolide, oblongulide, their natural 4-propyl analogue and the corresponding regioisomers.Demethylation and cyclisation of the tigloyl group gave inophyllums C and E, tomentolides A and B, and calanolide D.Sodium boranuide reduction of the 2,3-dimethylchromanone ring afforded inophyllums A, B, D and P, soulattrolide, calanolides A-C, costatolide, and cordatolides A and B.The structures of calanolides C and D, oblongulide and apetatolide have been reassigned.The previously unknown stereochemistry about the 2,3-dimethylchromanone ring of tomentolides A and B has been established as trans.

Synthesis of the calophyllum coumarins

Synthetic routes leading to the synthesis of the natural 4-alkyl and 4- phenyl coumarins isolated from Calophyllum sp. are reported. The reported structures of calanolides C and D and oblongutide are incorrect and have been corrected by unambiguous synthesis.

TWO CHEMICALLY DISTINCT GROUPS OF CALOPHYLLUM SPECIES FROM SRI LANKA

Key Word Index-Chalophyllum species; Guttiferae; (+)-cis-dihydroinophyllolide; inophyllum A; (-)-trans-dihydroinophyllolide; soulattrolide; calozeylanic acid.The leaf extracts of Calophyllum moonii and C. walkeri were investigated.The former contained neoflavonoids whereas the latter had calozeylanic acid.Distribution of natural products in the leaf extracts of seven Calophyllum species has been reviewed and the existence of two chemically distinct groups in Calophyllum species has been recognized.