245648-29-7

Upstream product

• 67-56-1 methanol 
• 245648-28-6 (S)-benzyl 2-(((tert-butyldiphenylsilyl)oxy)methyl)-5-oxopyrrolidine-1-carboxylate 
• 245674-39-9 (5S)-1-(benzyloxycarbonyl)-5-[(tert-butyldiphenylsilyloxy)methyl]-2-hydroxypyrrolidine 
• 17342-08-4 (S)-Pyroglutaminol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 132974-83-5 (5S)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]pyrrolidin-2-one 

Downstream Products

• 245648-30-0 (5S,2'S,5'S)-1'-benzyloxycarbonyl-5'-diphenyltert-butylsilyloxymethyl-2'-pyrrolidinyl-5-methylfuran-2(5H)-one 
• 245648-31-1 (5R,2'S,5'S)-1'-benzyloxycarbonyl-5'-diphenyltert-butylsilyloxymethyl-2'-pyrrolidinyl-5-methylfuran-2(5H)-one 
• 1400145-08-5 benzyl (2S,5S)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-(5-oxo-2,5-dihydrofuran-2-yl)pyrrolidine-1-carboxylate 
• 1400145-09-6 benzyl (2S,5S)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-(5-oxo-2,5-dihydrofuran-2-yl)pyrrolidine-1-carboxylate 
• 245648-33-3 (5R,2'S,5'S)-5'-diphenyltert-butylsilyloxymethyl-2'-pyrrolidinyl-5-methyltetrahydrofuran 

Relevant academic research and scientific papers

Total synthesis of (-)-sessilifoliamide J

An efficient synthesis of the Stemona alkaloid (-)-sessilifoliamide J (1) in 12 steps and 7.7% overall yield from the known building block 8 is presented. The synthesis features the Corey lactonization reaction and a highly diastereoselective α-methylation reaction to build the spirolactone moiety.

Synthesis of highly functionalized 2,5-disubstituted pyrrolidines via an aza-Morita-Baylis-Hillman-type reaction

An aza-Morita-Baylis-Hillman-type reaction of Michael acceptors with 5-substituted cyclic N,O-acetals derived from pyrrolidines has been investigated. It has been found that the combination of Me2S and TMSOTf work well with unhindered and reactive enals and enones whilst the use of quinuclidine and TMSOTf is superior for more hindered Michael acceptors. The reactions lead to 2,5-trans-disubstituted pyrrolidines with good to excellent diastereoselectivity. The origin of the selectivity is discussed.

Vinylogous Mannich reactions. Stereoselective formal synthesis of pumiliotoxin 251D

A concise synthesis of (-)-3, a known precursor of pumiliotoxin 251D, has been completed using a vinylogous Mannich reaction as a key construction. Silyloxyfuran 10 added to methoxypyrrolidine 20 in the presence of TMS-OTf to give a mixture (4.8:1) of 21 and 22 in 57% yield. Reduction and global deprotection of 21 afforded the bicyclic lactam 23. Raney Nickel mediated extrusion of the hydroxymethyl group from 23 gave (-)-3.