30801-12-8

Upstream product

• 67-56-1 methanol 
• 16633-27-5 (5S,9S,10S)-labda-8⁽¹⁷⁾,13-diene-15-al 
• 1067-74-9 Methyl diethylphosphonoacetate 
• 66971-94-6 (1R,4aR,8aR)-2-methylene-1-(3-oxobutyl)-5,5,8a-trimethyldecahydronaphthalene 
• 10266-75-8 4-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydronaphthalen-1-yl)butan-2-one 
• 314049-55-3 (1S,2S,4aS,8aS)-2-hydroxy-5,5,8a-trimethyldecahydronaphthalen-1-ylmethyl (S)-1-tert-butoxycarbonyl-pyrrolidine-2-carboxylate 
• 142037-79-4 andrographolide 
• 1234554-78-9 3α-hydroxy-13-oxo-15,16-dinor-ent-labda-8(17)-ene 
• 727723-06-0 2-((4aR,6aS,7R,10aS,10bR)-3,3,6a,10b-tetramethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)acetaldehyde 
• 20784-69-4 eperusaeure 
• 314049-59-7 (1R,2R,4aR,8aR)-2-hydroxy-5,5,8a-trimethyldecahydronaphthalen-1-ylmethyl (S)-1-tert-butoxycarbonyl-pyrrolidine-2-carboxylate 
• 13008-80-5 (13S)-5β,9β,10α-Labd-8(20)-en-15-saeure-methylester; Eperusaeure-methylester 
• 1034-49-7 (bromomethyl)triphenyl phosphonium bromide 

Downstream Products

• 126569-93-5 (4aR,5S,8aR)-6-[1-Bromo-meth-(E)-ylidene]-1,1,4a-trimethyl-5-((E)-3-methyl-5-trityloxy-pent-3-enyl)-decahydro-naphthalene 
• 191274-20-1 (E)-3-Methyl-5-((1R,4aR,8aR)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-pent-2-enoic acid (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 20257-75-4 5-(2-methylene-5,5,8a-trimethyl-(1R,4aR,8aR)-decahydronaphthalen-1-yl)-3-methylpent-2E-enoic acid 

Relevant academic research and scientific papers

Antitubercular activity increase in labdane diterpenes from Copaifera oleoresin through structural modification

The labdane diterpenes copalic acid, 3β-acetoxy-copalic acid, 3β-hydroxy-copalic acid and ent-agathic acid were isolated from Copaifera langsdorffii oleoresin. These four compounds were submitted to structural modifications by reduction with hydrogen/palladium, esterification with diazomethane, esterification with methanol/sulfuric acid and conversion into sodium salt, furnishing 15 compounds. All compounds were assayed in vitro against Mycobacterium tuberculosis (H37Rv, ATCC 27294). The four compounds displayed minimum inhibitory concentration (MIC) value of 125 μg mL-1, and were not considered active. A methylated derivative of compound 3β-hydroxy-copalic acid, and a sodium salt of copalic acid displayed MIC values of 25 μg mL-1 (71.7 μM) and 6.25 μg mL-1 (19.2 μM), respectively. The sodium salt of copalic acid stood out by displaying similar activity in comparison with streptomycin (MIC 6.25 μg mL-1) and a better activity compared to μM value of pyrazinamide (MIC 3.12 μg mL-1; 25.34 μM). Therefore, the methylated derivative of compound 3β-hydroxy-copalic acid and the sodium salt of copalic acid should be considered for further studies.

Copalic acid analogs down-regulate androgen receptor and inhibit small chaperone protein

Copalic acid, one of the diterpenoid acids in copaiba oil, inhibited the chaperone function of α-crystallin and heat shock protein 27?kD (HSP27). It also showed potent activity in decreasing an HSP27 client protein, androgen receptor (AR), which makes it

Synthesis of (-)-agathic acid and (-)-copalic acid from andrographolide via a regioselective Barton-McCombie reaction

The first synthesis of the ent-labdane diterpenoid (-)-agathic acid (1) with antibacterial activity is described. A chiral pool approach was employed with a linear sequence of 14 steps starting from readily available and inexpensive andrographolide. The regioselective deoxygenation in terms of Barton-McCombie free radical reaction completed a key step in the synthesis. (-)-Copalic acid (2), an analogue of (-)-agathic acid, has been conveniently synthesized from the key intermediate 7 in five steps.

Total synthesis of both enantiomers of copalol via optical resolution of a general synthetic intermediate for drimane sesquiterpenes and labdane diterpenes

The total synthesis of both enantiomers of copalol (6) was accomplished via the optical resolution of a racemic diol [(±)-4] which is a general synthetic intermediate for drimane sesquiterpenes and labdane diterpenes. Esterification between (±)-4 and Boc-L-proline gave the diastereomeric pair of monoesters (5a and 5b) which could be readily separated by flash column chromatography. PDC-oxidation of the resolved 5a and 5b, and subsequent β-elimination gave optically active enones (9 and ent-9). Both enones were respectively converted into (+)-6 in 36% yield and (-)-6 in 26% yield in five steps: (1) Sakurai reaction (TiC14-promoted conjugate addition of allylsilane), (2) Wittig methylenation, (3) Wacker oxidation, (4) Horner-Emmons reaction, and (5) DIBAL-H reduction. (C) 2000 Elsevier Science Ltd.

Stereochemistry of the cyclization-rearrangement of (+)-copalyl diphosphate to (-)-abietadiene catalyzed by recombinant abietadiene synthase from Abies grandis

(equation presented) Syntheses and enzymatic cyclizations of 8α,hydroxy-17-nor copalyl diphosphate (8a), (15R)-[15-2H1] 8b, and (15R,17E)-[15-3H1,17-2H1] copalyl diphosphate ([2H,3H] 2) catalyzed by recombinant abietadiene synthase (rAS) gave 17-nor manoyl oxide (9a), (16E)-[16-2H1] 9b, and (15S,16R)-[16-2H1,16-3H1] abietadiene ([2H1,3H1] 4), respectively. These and other results indicate that conversion of CPP (2) to abietadiene (4) occurs by anti SN′ cyclization to a sandaracopimar-15-en-8-yl carbocation intermediate (13+, 13β-methyl)' followed by hydrogen transfer and methyl migration suprafacially on the si face of the vinyl group.

The Optical Rotation of Some C15-Oxygenated Labda-8(17),13-dienes

A range of C15-oxygenated labda-8(17),13-dienes has been synthesized optically pure to provide reference data for comparisons with naturally occuring compounds.

Synthetic Routes to some Isotopically Labelled Intermediates for Diterpenoid Biosynthesis

The exo-15-hydrogen of ent-kauren can be exchanged through a reversible ene reaction in a convention and efficient procedure which has the potential for giving high specific activity (3)H-labeling.Copalol, the (Z)-double bond stereoisomer, and the allylic alcohol isomers ent-manool and ent-epimanool have been obtained through divergent synthetic pathways involving a 15,16-bisnor ketone intermediate.These pathways have also allowed the four compounds to be obtained with (14)C-labelling.A method, involving a Wittig reaction to form a vinyl bromide intermediate, has been developed for obtaining copalol, as the trityl ether derivative, with stereospecific isotopic labelling of one or the other of the hydrogens of the exocyclic methylene group.

SYNTHESIS OF (+)-TRICYCLOHEXAPRENOL, A POSSIBLE PRECURSOR OF A FAMILY OF TRICYCLIC GEOTERPANES, AND SYNTHESIS OF AN ISOMER.

A synthesis of (+)-tricyclohexaprenol 2 starting from isocopalenol 8 and a synthesis of its isomer 4 starting from ent-(14αH)-isocopalenol 26 are described.

Stereoselective Synthesis of the Novel Marine Diterpene (+)-Isoagatholactone

The synthesis of (+)-isoagatholactone (1) from (+)-manool (4) via the key intermediate ent-methyl isocopalate (2) is described.