339291-77-9

Upstream product

• 339291-61-1 2-[(2S,4aR,5S,7aR)-2-(4-Methoxy-phenyl)-5-methyl-hexahydro-cyclopenta[1,3]dioxin-5-yl]-ethanol 
• 339291-60-0 cyclopenta-1,3-dioxin-5-acetic acid, hexahydro-2-(p-methoxybenzylidene)-5-methyl, methyl ester, (2S,4R,5S,7R) 
• 339291-64-4 (Z)-4-[(1S,2R,3R)-2-Hydroxymethyl-3-(4-methoxy-benzyloxy)-1-methyl-cyclopentyl]-2-methyl-but-2-en-1-ol 
• 339291-67-7 (2E,4E)-5-[(1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-penta-2,4-dienoic acid methyl ester 
• 339291-68-8 (2E,4E)-5-[(1S,2S,5R)-2-((Z)-4-Hydroxy-3-methyl-but-2-enyl)-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-penta-2,4-dienoic acid methyl ester 
• 339291-65-5 [(1R,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-methanol 
• 339291-69-9 (2E,4E)-5-[(1S,2S,5R)-2-((Z)-4-Chloro-3-methyl-but-2-enyl)-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-penta-2,4-dienoic acid methyl ester 
• 339291-66-6 (1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentanecarbaldehyde 
• 339291-63-3 (Z)-4-[(2S,4aR,5S,7aR)-2-(4-Methoxy-phenyl)-5-methyl-hexahydro-cyclopenta[1,3]dioxin-5-yl]-2-methyl-but-2-enoic acid ethyl ester 
• 2403-58-9 4-methoxybenzaldehyde diethylacetal 
• 339291-70-2 (2E,4E)-5-[(1S,2S,5R)-2-((Z)-4-Chloro-3-methyl-but-2-enyl)-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-penta-2,4-dien-1-ol 

Downstream Products

• 339291-78-0 (3E,5E)-6-[(1S,2S,5R)-2-((Z)-4-Chloro-3-methyl-but-2-enyl)-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-2-hydroxy-hexa-3,5-dienenitrile 

Relevant academic research and scientific papers

Studies toward the total synthesis of clavulactone

Synthetic studies directed toward a total synthesis of clavulactone are reported. In light of the analysis made in our previous work, cyclopentane 4a (a key intermediate in the present work) was synthesized through a radical-mediated ring closure of a rationally designed substrate 25. Using HWE reactions, the lower and upper side-chains of 4a were converted into an allyl chloride and an allyl cyanohydrin, respectively. Subsequent treatment of the allyl chloride/cyanohydrin in a highly diluted THF solution with sodium bis(trimethylsiliyl)amide led to intramolecular alkylation and thus completed a major endeavor in synthesizing the dolabellane framework, construction of the eleven-membered ring. SmI2-mediated lactonization as a model reaction for the formation of the α,β-unsaturated δ-lactone segment of clavulactone is also described.