329184-69-2

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 329184-68-1 [2-(tert-butyldiphenylsilanyloxy)ethyl]-[(S)-(3Z,6Z)-10-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)-1-propyldeca-3,6-dienyl]amine 
• 170956-17-9 (S)-1-[(4-methylphenyl)sulfonyl]-2-propylaziridin 
• 329184-63-6 4-methyl-N-[(S)-1-propyl-5-(tetrahydropyran-2-yloxy)pent-3-ynyl]benzenesulfonamide 
• 329184-65-8 N-[(S)-5-bromo-1-propylpent-3-ynyl]-N-[2-(tert-butyl-diphenylsilanyloxy)ethyl]-4-methylbenzenesulfonamide 
• 329184-64-7 N-[2-(tert-butyldiphenylsilanyloxy)ethyl]-4-methyl-N-[(S)-1-propyl-5-(tetrahydropyran-2-yloxy)pent-3-ynyl]benzenesulfonamide 
• 329184-67-0 N-[2-(tert-butyldiphenylsilanyloxy)ethyl]-4-methyl-N-[(S)-(3Z,6Z)-10-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)-1-propyldeca-3,6-dienyl]benzenesulfonamide 
• 329184-66-9 N-[2-(tert-butyldiphenylsilanyloxy)ethyl]-4-methyl-N-[(S)-10-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)-1-propyldeca-3,6-diynyl]benzenesulfonamide 

Downstream Products

• 329184-78-3 (S)-(5Z,8Z)-11-[tert-butoxycarbonyl-(2-{(S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienyloxy}ethyl)amino]tetradeca-5,8-dienoic acid allyl ester 
• 329184-80-7 (S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienoic acid 2-[tert-butoxycarbonyl-((S)-(Z)-10-carboxy-1-propyldec-6-enyl)amino]ethyl ester 
• 329184-81-8 (S)-(5Z,8Z)-11-[tert-butoxycarbonyl-(2-{(S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienyloxy}ethyl)amino]tetradeca-5,8-dienoic acid 
• 329184-72-7 (S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienoic acid allyl ester 
• 329184-70-5 (S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienoic acid 

Relevant academic research and scientific papers

Synthesis of unsaturated polyazamacrolides from the ladybird beetle Subcoccinella vigintiquatuorpunctata

The pupal defensive secretion of the ladybird beetle Subcoccinella vigintiquatuorpunctata consists of a mixture of macrocyclic polyamines (polyazamacrolides, PAMLs) dominated by three dimeric, 30-membered bislactones (1, 2, and 3), which represent the three possible head-to-tail combinations of the two building blocks (S)-(Z)-11-(2-hydroxyethylamino)-5-tetradecenoic acid (4) and (S)-(5Z,8Z)-11-(2-hydroxyethylamino)-5,8-tetradecadienoic acid (5). We now report the synthesis of these three alkaloids via a route involving the nucleophilic opening of a chiral aziridine as a common step.