A short formal synthesis of (±)-perhydrohistrionicotoxin
The reaction of a silyl enol ether bearing a nitrogen atom with a hemiacetal vinylog in the presence of a catalytic amount of boron trifluoride etherate led to the corresponding ketoaldehyde. The cyclisation of the ketoaldehyde into azaspiroenone and nitrogen deprotection was performed in basic medium. The N-benzylation of this enone gave the known key intermediate of total synthesis of (±)-perhydrohistrionicotoxin. Georg Thieme Verlag Stuttgart.
Deyine, Abdallah,Poirier, Jean-Marie,Duhamel, Pierre
Synthesis of alkaloid analogues from β-amino alcohols by β-fragmentation of primary alkoxyl radicals
The fragmentation of primary alkoxyl radicals is usually a minor process with respect to hydrogen abstraction and other competing reactions. However, when β-amino alcohols were used as substrates, the scission proceeded in good to excellent yields and no side reactions were observed. The fragmentation can be coupled with an allylation or alkylation reaction, to give alkaloid analogues and functionalized nitrogen heterocycles. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
DERIVATIVES OF HETEROCYCLIC α-IMINOCARBOXYLIC ACIDS. 4. REDUCTION OF N-ALKOXYCARBONYL DERIVATIVES OF α-IMINOCARBOXYLIC ACIDS.
When N-methoxycarbonyl and N-benzoxycarbonyl derivatives of methyl esters of aziridine-2-carboxylic acid, L-proline, L-thioproline, and pipecolic acid interact with NaBH4 in tert-butanol/methanol, the products of reduction of the C-methoxycarbonyl group o
Nurdinov, R.,Liepin'sh, E. E.,Kalvin'sh, I. Ya.
p. 1352 - 1357
(2007/10/02)
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