1131783-60-2

Upstream product

• 1131783-58-8 ethyl 2-((1S,2S,5S,6S)-2-allyl-6-(tert-butyldimethylsilyloxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-5-methyl-3-oxocyclohexyl)acetate 
• 2960-66-9 4-oxo-but-2-enoic acid ethyl ester 
• 1131783-70-4 (4R,5S,E)-ethyl 4-(tert-butyldimethylsilyloxy)-5-methylhepta-2,6-dienoate 
• 15252-44-5 1-amino-pent-4-yne 
• 2396-84-1 (2E,4E)-ethyl hexa-2,4-dienoate 
• 1131783-54-4 (2E,4S,5S,8E)-ethyl 4-(tert-butyldimethylsilyloxy)-8-(1-(1-(4-methoxyphenyl)ethyl)pyrrolidin-2-ylidene)-5-methyl-7-oxooct-2-enoate 
• 1131783-72-6 (4S,5S,E)-ethyl 4-((tert-butyldimethylsilyl)oxy)-5-methyl-7-oxohept-2-enoate 
• 1417600-97-5 C₂₆H₄₅NOSn 
• 1131783-52-2 (3S,4S,E)-4-((tert-butyldimethylsilyl)oxy)-7-ethoxy-3-methyl-7-oxohept-5-enoic acid 
• 6097-07-0 N-(pent-4-ynyl)phthalimide 
• 1131783-50-0 (4S,5S,E)-ethyl 4-((tert-butyldimethylsilyl)oxy)-7-hydroxy-5-methylhept-2-enoate 
• 14267-92-6 1-chloro-4-pentyne 
• 1131783-48-6 (4R,5S,E)-ethyl 4-hydroxy-5-methylhepta-2,6-dienoate 

Downstream Products

• 1131783-62-4 ethyl 2-((1S,2S,5S,6S)-2-allyl-6-(tert-butyldimethylsilyloxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-5-methyl-3-(methanesulfonyloxy)cyclohexyl)acetate 
• 1131783-64-6 ethyl 2-((1S,2S,5S,6S)-6-(tert-butyldimethylsilyloxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-2-(3-hydroxypropyl)-5-methyl-3-(methanesulfonyloxy)cyclohexyl)acetate 

Relevant academic research and scientific papers

Total synthesis of the lycopodium alkaloid serratezomine a using free radical-mediated vinyl amination to prepare a β-stannyl enamine linchpin

Serratezomine A is a member of the structurally diverse class of compounds known as the Lycopodium alkaloids. The key supporting studies and successful total synthesis of serratezomine A are described in this account. Significant features of the synthesis include the first application of free radical mediated vinyl amination and Hwu's oxidative allylation in a total synthesis and an intramolecular lactonization via a transannular SNi reaction. Minimal use of protecting groups and the highly diastereoselective formation of a hindered, quaternary stereocenter using an umpolung allylation are also highlights from a strategy perspective. Observation of quaternary carbon epimerization via a retro-Mannich/Mannich sequence highlights the additional challenge presented by the axial alcohol at C8 in serratezomine A.