D. V. Nedopekin

Transformation of 20-Hydroxyecdysone Acetonides into Podecdysone B

Hydrogenation of 20-hydroxyecdysone 2,3:20,22-diacetonide and 20,22-acetonide over palladium catalyst yields podecdysone B 20,22-acetonide. Acid hydrolysis of the latter affords podecdysone B which is a natural phytoecdysteroid.

Orifluoroacetylation and dehydration of 20-hydroxyecdysone acetonides. Synthesis of stachisterone B

Orifluoroacetylation of the 25(OH)-group with subsequent dehydration of the 14(OH)-group takes place in the reaction of 20-hydroxyecdysone 20,22-acetonide and 2,3:20,22-diacetonide with trifluoroacetic anhydride in the presence of pyridine. Dehydration of the 14(OH)-group gives rise to stachisterone B derivatives, which are hydrolyzed to give the phytoecdysteroid stachisterone B.

New Derivatives of 20-Hydroxyecdyzone. Viticosterone E Synthesis

New 20,22-mono- and 2,3:20,22-diacetals of 20-hydroxyecdyzone were synthesized, and some thereof were applied to the synthesis of 25-O-acetyl-20-hydroxyecdyzone (viticosterone E).

Ozonides with the tetrahydroquinoline and dehydroabietic fragments

Acid-catalyzed three-component condensation of methyl 12-aminodehydroabietate, aromatic aldehydes, and cyclopentadiene gave methyl (4R)-4-aryl-6-isopropyl-10,13a-dimethyl-3a,4,5,8,9,9a,10,11,12,13,13a,13d-dodecahydro-3H-cyclopenta[c]naphtho[1,2-f]quinoline-10-carboxylates and their (4S)-diastereomers. Ozonolysis of the double bond in their N-trifluoroacetyl derivatives synthesized from the (4R)-diastereomers afforded the corresponding ozonides with the (1S,4R,5aS,6R,11aR,12R,15aS,15dR)-configuration.

Cyclocondensation of methyl 12-aminodehydroabietate with aldehydes and cyclopentadiene. Synthesis of tricyclic diterpenoide fused to tetrahydroquinoline

Three-component cyclocondensation of methyl 12-aminodehydroabietate with cyclopentadiene and formaldehyde or acetaldehyde under acid catalysis afforded polysubstituted naphthoquinoline derivatives with fused oxetanocyclopentane and cyclopentene fragments. Ozonation of the double bond in the N-trifluoroacetyl cyclopentene derivatives gave the corresponding ozonide.

Cyclocondensation of lower aliphatic aldehydes with arylamines and cyclopentadiene

Three-component condensation of lower aliphatic aldehydes (C1-C3) with arylamines and cyclopentadiene (the Povarov reaction) gave 3a,4,5,9b-tetrahydro-3H-cyclopenta[c]-quinolines. Ozonization of their N-trifluoroacetyl derivatives afforded the corresponding ozonides. Cyclocondensation of 4-fluoroaniline with formaldehyde and cyclopentadiene gave earlier unknown 2-fluoro-3b,6,6a,7,9,9a,10,12a-octahydrobenzo[i,j]dicyclopenta[b,g]quinolizine.