29079-30-9Relevant academic research and scientific papers
Formal Synthesis of Indolizidine and Quinolizidine Alkaloids from Vinyl Cyclic Carbonates
Cristòfol, àlex,B?hmer, Christian,Kleij, Arjan W.
, p. 15055 - 15058 (2019)
Cyclic carbonates have long been considered relatively inert molecules acting as protecting groups in complex multistep synthetic routes. This study shows that a concise, yet modular synthesis of indolizidine and quinolizidine alkaloids can be developed from vinyl-substituted cyclic carbonate (VCC) intermediates. Through a highly stereoselective palladium-catalyzed allylic alkylation reaction, these alkaloid motifs can be assembled in four synthetic and only two column purification steps. The combined results help to further advance functionalized cyclic carbonates as useful and reactive intermediates in natural product synthesis.
Superacid-promoted synthesis of indolizidine derivatives
Kennedy, Sean,Kethe, Anila,Qarah, Ahmad,Klumpp, Douglas A.
, p. 1932 - 1935 (2018/04/16)
A series of amido-acetals were reacted with the Br?nsted superacid, CF3SO3H, to provides indolizidine derives by a cyclization cascade. A mechanism is proposed involving formation of a vinylogous enol which undergoes a 6π-electrocycl
Synthesis of (+)-Ipalbidine Based on 6-exo-trig Radical Cyclization of a β-Amino Radical
Chea, JongMyoung,Clive, Derrick L. J.
, p. 10294 - 10298 (2015/11/03)
N-Boc (S)-proline was converted into (2S)-2-[(phenylselanyl)methyl]pyrrolidine, which was alkylated on nitrogen with 2-bromo-1-(4-methoxyphenyl)ethan-1-one. Reaction with vinyllithium, 6-exo-trig radical cyclization (Bu3SnH, AIBN, PhMe, 110 °C), dehydration (P2O5, H3PO4), and demethylation (BBr3) gave (+)-ipalbidine with ee >99%.
A synthesis of (±)-ipalbidine using sulfur-controlled 6-exo selective radical cyclization of α-phenylthio amide
Ikeda, Masazumi,Shikaura, Jiro,Maekawa, Noriko,Daibuzono, Kaori,Teranishi, Hirotaka,Teraoka, Yoshiko,Oda, Norio,Ishibashi, Hiroyuki
, p. 31 - 34 (2007/10/03)
A synthesis of (±)-ipalbidine (1) has been achieved using Bu3SnH- mediated 6-exo selective radical cyclization of 2-[3-(phenylthio)prop-2- enyl]-N-[α(p-methoxyphenyl)-α-(phenylthio)acetyl]pyrrolidine (15) as a key step.
A Concise Total Synthesis of (+/-)-Ipalbidine by Application of the Aldimine-Diene Cyclocondensation Reaction
Danishefsky, Samuel J.,Vogel, Claus
, p. 3915 - 3916 (2007/10/02)
The scope of the diene-imine cyclocondensation reaction has been extended to the unstable Δ1-pyrroline.Cyclocondensation of this compound with the silylketene acetal derived from ethyl 2-p-anisyl-3-methylcrotonate provides the basis for a rapid
SYNTHESIS OF THE ALKALOIDS JULANDINE AND IPALBIDINE - USE OF SILICON (IV) CHLORIDE
Cragg, John E.,Hedges, Stuart H.,Herbert, Richard B.
, p. 2127 - 2130 (2007/10/02)
Titanium (IV) chloride and silicon (IV) chloride with high oxygen affinity are the best Lewis acid catalysts, of a number tested, for cyclisation of an enamine-ketone (1) leading to the alkaloid, julandine (2); cyclisation of (6) in methanol solution without catalyst yields O-methylipalbidine (7).
