77733-65-4

Upstream product

• 51207-70-6 (2S)-N-Benzyloxycarbony-2-(1'-methylethenyl)pyrrolidine 
• 123032-80-4 (S)-2-isopropenylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 1305339-29-0 C₉H₁₃F₃INO₂ 
• 1305339-30-3 C₉H₁₂F₃NO 
• 5211-23-4 N-carbobenzyloxy-L-proline methyl ester 
• 51207-68-2 (2S)-N-Benzyloxycarbony-2-(1'-hydroxy-1'-methylethyl)pyrrolidine 

Downstream Products

• 116505-87-4 (S)-2-((E)-(1S,5R,9S)-9-Benzyloxy-1-hydroxy-1,5,8-trimethyl-undec-7-en-3-ynyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 98088-43-8 (1S,7aS)-1-((2Z,6E)-(S)-8-Benzyloxy-4,7-dimethyl-2-trimethylsilanyl-deca-2,6-dienyl)-1-methyl-tetrahydro-pyrrolo[1,2-c]oxazol-3-one 
• 90246-44-9 (1S ,7aS)-tetrahydro-1-methyl-1-<6-(benzyloxy)-4(R)-methyl-2-(trimethylsilyl)-2(Z)-hexenyl>-1H,3H-pyrrolo<1,2-c>oxazol-3-one 
• 182053-14-1 (S)-2-[(E)-(1S,5R)-1-Hydroxy-1,5-dimethyl-8-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-non-7-en-3-ynyl]-pyrrolidine-1-carboxylic acid benzyl ester 
• 67016-65-3 Pumiliotoxin B 
• 90246-45-0 (8S,8aS)-8-hydroxy-8-methyl-6(Z)-<4-(benzyloxy)-2(R)-methylbutylidene>octahydroindolizidine 
• 90246-46-1 (1S,7aS)-1-((Z)-(R)-6-Benzyloxy-4-methyl-2-trimethylsilanyl-hex-2-enyl)-1-methyl-tetrahydro-pyrrolo[1,2-c]oxazole 
• 90246-49-4 (8S,8aS)-8-hydroxy-8-methyl-6(Z)-<6-oxo-2(R),5-dimethyl-7(R)-(tert-butyldiphenylsiloxy)-4(E)-octenylidene>octahydroindolizidine 
• 116505-88-5 (E)-(2S,6R,10S)-10-Benzyloxy-6,9-dimethyl-2-(S)-pyrrolidin-2-yl-dodec-8-en-4-yn-2-ol 
• 98088-45-0 (8S,8aS)-8-hydroxy-8-methyl-(6Z)-<(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene>octahydroindolizidine 
• 116561-36-5 (8S,8aS)-8-hydroxy-8-methyl-(6E)-<(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-1-iodo-4-octenylidene>octahydroindolizine 
• 116505-82-9 (S)-2-((S)-1-Hydroxy-1-methyl-oct-3-ynyl)-pyrrolidine-1-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Enantioselective formal total synthesis of the Dendrobatidae frog toxin, (+)-pumiliotoxin B, via O-directed alkyne free radical hydrostannation

Herein we describe our application of the O-directed free radical hydrostannation of disubstituted alkylacetylenes (with Ph3SnH and Et3B) to the (+)-pumiliotoxin B total synthesis problem. Specifically, we report on the use of this method in the synthesis of the Overman alkyne 8, and thereby demonstrate the great utility of this process in a complex natural product total synthesis setting for the very first time. We also report here on a new, stereocontrolled, and highly practical enantioselective pathway to Overman's pyrrolidine epoxide partner 9 for 8, which overcomes the previous requirement for use of preparative HPLC to separate the 1:1 mixture of diastereomeric epoxides that was obtained in the original synthesis of 9.