65620-67-9Relevant academic research and scientific papers
An asymmetric synthesis of (+)-isonitramine by 'triple allylic strain-controlled' intramolecular S(N)2' alkylation
Kim,Choi,Hong,Park,Kim
, p. 1433 - 1434 (1996)
The spirocyclic alkaloid (+)-isonitramine (1) has been synthesized in a stereoselective manner utilizing a novel 'triple allylic strain-controlled' intramolecular lactam enolate S(N)2' alkylation.
Enantioselective Total Synthesis of Nitraria Alkaloids: (+)-Nitramine, (+)-Isonitramine, (-)-Isonitramine, and (-)-Sibirine via Asymmetric Phase-Transfer Catalytic α-Allylations of α-Carboxylactams
Yang, Jewon,Park, Yohan,Yang, Sehun,Lee, Geumwoo,Ha, Min Woo,Kim, Mi-Hyun,Hong, Suckchang,Park, Hyeung-Geun
, p. 4375 - 4390 (2021/02/05)
Many optically active 2-azaspirocyclic structures have frequently been found in biologically active natural products. In particular, Nitraria alkaloids, (+)-nitramine, (+)-isonitramine, (-)-isonitramine, and (-)-sibirine, have stereogenicity on their quat
Highly enantioselective total synthesis of (+)-isonitramine
Park, Yohan,Lee, Young Ju,Hong, Suckchang,Lee, Myungmo,Park, Hyeung-Geun
, p. 852 - 854 (2012/04/05)
A new efficient enantioselective synthetic method of (+)-isonitramine is reported. (+)-Isonitramine was obtained in 12 steps (98% ee and 43% overall yield) from δ-valerolactam via enantioselective phase-transfer catalytic alkylation, Dieckman condensation
Platinum(II)-catalyzed cyclizations forming quaternary carbon centers, using enesulfonamides, enecarbamates, or enamides as nucleophiles
Harrison, Tyler J.,Patrick, Brian O.,Dake, Gregory R.
, p. 367 - 370 (2007/10/03)
(Chemical Equation Presented) Cyclic enesulfonamides, enecarbamates, or enamides tethered to an alkyne cyclize readily with use of platinum(II) chloride. This reaction generates quaternary-substituted carbon centers within simple spiro-fused or more compl
Synthesis of racemic nitramine, isonitramine and sibirine
Deyine, Abdallah,Poirier, Jean-Marie,Duhamel, Lucette,Duhamel, Pierre
, p. 2491 - 2493 (2007/10/03)
Condensation of enol ether 6 with methyl vinyl ketone led easily to ketoaldehyde 7 whose cyclisation afforded the azaspiranic enone 8, a key intermediate for the synthesis of the title alkaloids.
Stereoselective Synthesis of (+/-)-Isonitramine and (+/-)-Sibirine
Fujii, Masayuki,Kawaguchi, Koichi,Nakamura, Kaoru,Ohno, Atsuyoshi
, p. 1493 - 1496 (2007/10/02)
Spirocyclic alkaloids, (+/-)-isonitramine and (+/-)-sibirine were synthesized in high overall yields via a chemoselective reduction by Hantzsch ester (HEH), a coenzyme NADH model compound.
SYNTHESIS OF (+/-)-NITRAMINE, (+/-)-ISONITRAMINE AND (+/-)-SIBIRINE VIA DIELS-ALDER REACTIONS
Wanner, M.J.,Koomen, G.J.
, p. 2301 - 2304 (2007/10/02)
Diels-Alder reactions with N-protected methyleneglutarimides are used to construct the spiro-framework during the synthesis of the title alkaloids.
ASYMMETRIC SYNTHESIS XV: ENANTIOSPECIFIC SYNTHESIS OF (+) AND (-) ISONITRAMINES FROM A COMMON CHIRAL INTERMEDIATE.
Quirion, Jean-Charles,Grierson, David S.,Royer, Jacques,Husson, Henri-Philippe
, p. 3311 - 3314 (2007/10/02)
The enantiospecific synthesis of (+) and (-) isonitramines 7 has been achieved from a common chiral intermediate 5; this key compound was formed by condensation of two molar equivalents of glutaraldehyde with one mole of (-) phenylglycinol.
Synthesis of (+/-)-Nitramine and (+/-)-Isonitramine
Carruthers, William,Moses, Roger C.
, p. 1625 - 1628 (2007/10/02)
The alkaloids (+/-)-nitramine (1; R=H) and (+/-)-isonitramine (2; R=H) have been synthesized, employing an intramolecular Mannich rection to set up the spirocyclic ring system.
