329184-66-9

Upstream product

• 89276-37-9 1-(pent-4-ynyl)-4-methyl-2,6,7-trioxabicyclo<2.2.2>octane 
• 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 
• 329184-63-6 4-methyl-N-[(S)-1-propyl-5-(tetrahydropyran-2-yloxy)pent-3-ynyl]benzenesulfonamide 
• 170956-17-9 (S)-1-[(4-methylphenyl)sulfonyl]-2-propylaziridin 

Downstream Products

• 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 
• 329184-68-1 [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 
• 329184-70-5 (S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)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 
• 329184-69-2 [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]carbamic acid dimethylethyl 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 
• 329184-80-7 (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 
• 329184-78-3 (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 

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.