312929-13-8

Upstream product

• 53102-99-1 di(pent-4-en-1-yl)magnesium 
• 170956-17-9 (S)-1-[(4-methylphenyl)sulfonyl]-2-propylaziridin 
• 6600-40-4 L-Norvaline 
• 22724-81-8 L-norvalinol 
• 1119-51-3 bromopentene 
• 62421-32-3 (2S)-2-[(p-tolylsulfonyl)amino]-1-[(p-tolylsulfonyl)oxy]pentane 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 189251-20-5 (7S)-7-({2-[(tert-butyl)dimethylsilyloxy]ethyl}(p-tolylsulfonyl)amino)dec-1-ene 
• 147363-82-4 (S)-epilachnene 

Relevant academic research and scientific papers

Synthesis of macrocyclic insect-derived alkaloids

Macrocyclic lactonic alkaloids found in the pupal secretions of two species of a coccinellid beetle (genus Epilachna) were prepared in enantiomerically pure form via an efficient synthetic route using enantiomerically pure α-amino acids as chiral-pool starting materials. Macrocycles with rings containing up to 98 atoms were synthesized in good yield using Mukaiyama's macrolactonization conditions.

Absolute configuration of insect-produced epilachnene

Samples of (X) and (S)-epilachnene [(5Z)-11-propyl-12-azacyclotetradec-5-en olide] were synthesized from (R) and (S)-norvaline. The diastereomeric α-methoxy-α-trifluoromethylphenylacetyl amides of these synthetic samples, prepared using (S) α-methoxy-α-trifluoromethylphenylacetyl chloride, were well resolved by gas chromatography. Analogous derivatization and gas chromatographic analysis of a sample of epilachnene from the pupal secretion of the coccinellid beetle, Epilachna varivestis, established that the natural product is (S)-epilachnene.