51493-69-7

Usage

InChI:InChI=1/C20H28O4/c1-11(2)16-6-13-7-19(10-22)15-5-4-12(3)14(15)8-18(13,9-21)20(16,19)17(23)24/h6,10-15,21H,4-5,7-9H2,1-3H3,(H,23,24)/t12-,13+,14-,15-,18+,19+,20-/m1/s1

Upstream product

• 528878-85-5 ((3S,3aS,4S,7R,7aS)-3-Methoxymethoxymethyl-3a,4,7,7a-tetrahydro-3H-4,7-methano-inden-1-yloxy)-trimethyl-silane 
• 896435-43-1 C₂₂H₃₀O₄ 
• 528878-74-2 methyl (1S,3aR,4S,7R,7aS,1'R,2'R,5'R)-1-[2'-(1''-formylvinyl)-5'-methylcyclopentylmethyl]-1-hydroxymethyl-3-isopropyl-3a,4,7,7a-tetrahydro-1H-4,7-methanoindene-2-carboxylate 
• 1499201-69-2 xylarinonericin C 
• 528878-94-6 methyl (5S,1'R,2'R,5'R)-5-methoxymethoxymethyl-5-[{2'-(1''-(methoxymethoxymethyl)vinyl)-5'-methylcyclopentyl}methyl]-2-trifluoromethylsulfonyloxycyclopenta-1,3-diene-1-carboxylate 
• 528878-92-4 (3'R,3a'S,4'R,7'S,7a'R,1''R,2''R,5''R)-3'-methoxymethoxymethyl-3'-[{2''-(1'''-(methoxymethoxymethyl)vinyl)-5''-methylcyclopentyl}methyl]-2',3',3a',4',7',7a'-hexahydro-1H-4',7'-methanoindene-1'-spiro-2-[1,3]dioxolane 
• 528878-91-3 (3'R,3a'S,4'R,7'S,7a'R,1''R,2''R,5''R)-3'-hydroxymethyl-3'-[2''-(1'''-methoxymethoxymethylvinyl)-5''-methylcyclopentylmethyl]-2',3',3a',4',7',7a'-hexahydro-1H-4',7'-methanoindene-1'-spiro-2-[1,3]dioxolane 
• 528878-71-9 (1'R,3a'R,4'S,7'R,7a'S,1''R,2''R,5''R)-1'-[2''-(1'''-methoxymethoxymethylvinyl)-5''-methylcyclopentylmethyl]-2',3',3a',4',7',7a'-hexahydro-1H-4',7'-methanoindene-1'-cyano-3'-spiro-2-[1,3]dioxolane 
• 528878-72-0 (3R,3aS,4R,7S,7aR,1'R,2'R,5'R)-3-methoxymethoxymethyl-3-[{2'-(1''-(methoxymethoxymethyl)vinyl)-5'-methylcyclopentyl}methyl]-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoinden-1-one 
• 528878-90-2 (1'R,3a'R,4'S,7'R,7a'S,1''R,2''R,5''R)-1'-[2''-(1'''-methoxymethoxymethylvinyl)-5''-methylcyclopentylmethyl]-2',3',3a',4',7',7a'-hexahydro-1H-4',7'-methanoindene-1'-formyl-3'-spiro-2-[1,3]dioxolane 
• 528878-81-1 methyl (5S,1'R,2'R,5'R)-2-isopropyl-5-methoxymethoxymethyl-5-[{2'-(1''-(methoxymethoxymethyl)vinyl)-5'-methylcyclopentyl}methyl]cyclopenta-1,3-diene-1-carboxylate 
• 847069-64-1 methyl (2S,1'R,2'R,5'R)-2-methoxymethoxymethyl-2-[{2'-(1''-(methoxymethoxymethyl)vinyl)-5'-methylcyclopentyl}methyl]-5-oxocyclopent-3-ene-1-carboxylate 
• 528878-82-2 methyl (5S,1'R,2'R,5'R)-5-hydroxymethyl-5-[{2'-(1''-hydroxyvinyl)-5'-methylcyclopentyl}methyl]-2-isopropylcyclopenta-1,3-diene-1-carboxylate 
• 528878-73-1 methyl (5S,1'R,2'R,5'R)-5-[2'-(1''-formylvinyl)-5-methylcyclopentylmethyl]-5-hydroxymethyl-2-isopropylcyclopenta-1,3-diene-1-carboxylate 

Downstream Products

• 525595-61-3 C₄₆H₇₂O₆ 
• 525595-69-1 C₃₉H₅₂O₆ 
• 525595-68-0 C₃₈H₅₀O₆ 
• 525595-63-5 C₃₈H₅₄O₆ 
• 525595-62-4 C₃₇H₅₂O₆ 
• 525595-65-7 C₃₆H₄₈O₆ 

Relevant academic research and scientific papers

Total synthesis of sordaricin

(Matrix presented) The total synthesis of sordaricin, the diterpene aglycone of an important class of antifungal compounds, is described. Two approaches were explored, the first of which utilized a possible biogenetic intramolecular [4 + 2] cycloaddition to form the complete carbon skeleton of the target molecule. A second approach using a tandem cycloreversion/intramolecular [4 + 2] cycloaddition sequence is also detailed.

Amide, cyclohexenone, and cyclohexenone-sordaricin derivatives from the endophytic fungus Xylaria plebeja PSU-G30

Six new compounds, two cyclohexenones, named xylariacyclones A (1) and B (2), three cyclohexenone-sordaricin derivatives, named xylarinonericins A-C (3-5), and one amide derivative, named xylariamide (6), together with 11 known compounds were isolated from the broth extract of the endophytic fungus Xylaria plebeja PSU-G30. The structures were elucidated by analyses of NMR spectroscopic data and chemical methods. Compounds 3-5 are novel and unusual sodaricin derivatives with an ester moiety at C-6 of the sordaricin skeleton. In addition, compound 5 has a unique feature with an ester unit instead of an ether group at C-19. They were evaluated for antifungal activity against Candida albicans ATCC90028 and Cryptococcus neoformans ATCC90113.

Synthesis of (-)-sordarin

The first total synthesis of (-)-sordarin (1) was accomplished exploiting the following key reactions: (i) Ag(I)-catalyzed oxidative radical cyclization of a cyclopropanol derivative leading to a bicyclo-[5.3.0]decan-3-one skeleton; (ii) Pd(0)-catalyzed i

Total synthesis of sordaricin

(Chemical Equation Presented) An enantioconvergent total synthesis of sordaricin (3), the diterpene aglycon of an important class of antifungal compounds, is described. Two approaches were explored, the first of which utilized a possible biogenetic intram

Sordaricin antifungal agents

Compounds based on sordaricin were prepared via organometallic addition onto a fully protected sordaricin aldehyde. The fungal growth inhibition profiles for these compounds were established and the results are presented here. The synthesis of homologated sordaricin as well as ether and ester derivatives is presented, and structural rearrangement products upon oxidation. These compounds were evaluated as agents to inhibit fungal growth.

Alkyl side-chain derivatives of sordaricin as potent antifungal agents against yeast

Sordarin (1) was converted to 5 and 6, which showed potent antifungal activity against yeast. A series of C1-C9 alkyl side-chain derivatives was prepared, from which it was found that the optimal activity occurred with C5. A comparison of side chains with different unsaturation showed that the cis- alkene was the most active. This result suggested that the folding of the side chains might be crucial for the optimal activity.