10438-97-8Relevant academic research and scientific papers
Bioinspired enantioselective synthesis of crinine-type alkaloids: Via iridium-catalyzed asymmetric hydrogenation of enones
Zuo, Xiao-Dong,Guo, Shu-Min,Yang, Rui,Xie, Jian-Hua,Zhou, Qi-Lin
, p. 6202 - 6206 (2017/08/29)
A bioinspired enantioselective synthesis of crinine-type alkaloids has been developed by iridium-catalyzed asymmetric hydrogenation of racemic cycloenones. The method features a biomimetic stereodivergent resolution of the substrates bearing a remote arylated quaternary stereocenter. Using this protocol, 24 crinine-type alkaloids and 8 analogues were synthesized in a concise and rapid way with high yield and high enantioselectivity.
TOTAL SYNTHESIS OF THE AMARYLLIDACEAE ALKALOID (+/-)-EPIELWESINE. THE IMPORTANCE OF VINYLSILANE STEREOCHEMISTRY IN IMINIUM ION-VINYLSILANE CYCLIZATIONS
Burk, Robert M.,Overman, Larry E.
, p. 205 - 225 (2007/10/02)
(+/-)-Epielwesine (9) was prepared in an efficient and completely stereocontrolled fashion in six steps and 28percent overall yield from commercially available 3,4-methylenedioxyphenylacetonitrile (15a).The key step is acid promoted cyclization of the (Z)
Synthesis of Sceletium and Amaryllidaceae Alkaloids, (+/-)-Mesembrine and (+/-)-Dihydromaritidine, (+/-)-Epidihydromaritidine, (+/-)-Elwesine, and (+/-)-Epielwesine
Hoshino, Osamu,Sawaki, Shohei,Shimamura, Naomi,Onodera, Akira,Umezawa, Bunsuke
, p. 2734 - 2743 (2007/10/02)
The alkylation of 2-arylcyclohexanones (12b and 6) with alkyl halides or acrylonitrile and 50percent aq. sodium hydroxide in the presence of a phase-transfer catalyst (18-crown-6) was found to give readily 2-alkyl-2-arylcyclohexanones (14 and 16) in fair
THE IMPORTANCE OF VINYLSILANE STEREOCHEMISTRY AND ?-? STABILIZATION IN IMINIUM ION-VINYLSILANE CYCLIZATIONS. A SHORT TOTAL SYNTHESIS OF THE AMARYLLIDACEAE ALKALOID (+/-)-EPIELWESINE.
Overman, Larry E.,Burk, Robert M.
, p. 5739 - 5742 (2007/10/02)
cis-3a-Aryl-2,3,3a,4,5,7a-hexahydro-1H-indoles 5 and 10 are formed in excellent yield from acid promoted cyclization of (Z)-vinylsilane imines 3 and 9.The failure of the corresponding (E)-vinylsilane isomer 4 to cyclize under similar condition demonstrate
