Synthesis of (±)-kainic acid by dearomatising cyclisation of a lithiated N-benzyl p-anisamide

Jonathan Clayden; Kirill Tchabanenko

doi:10.1039/A909325G

Synthesis of (±)-kainic acid by dearomatising cyclisation of a lithiated N-benzyl p-anisamide

Jonathan Clayden^*, Kirill Tchabanenko

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

60 Citations (Scopus)

Abstract

N-Benzyl p-anisamide 6, on lithiation with Bu(t)Li in the presence of HMPA, undergoes a stereoselective anionic cyclisation with loss of aromaticity to give a bicyclic enone which may be converted in nine steps to (±)-kainic acid.

Original language	English
Pages (from-to)	317-318
Number of pages	2
Journal	Chemical Communications
Issue number	4
Early online date	10 Feb 2000
DOIs	https://doi.org/10.1039/A909325G
Publication status	Published - 21 Feb 2000

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title = "Synthesis of (±)-kainic acid by dearomatising cyclisation of a lithiated N-benzyl p-anisamide",

abstract = "N-Benzyl p-anisamide 6, on lithiation with Bu(t)Li in the presence of HMPA, undergoes a stereoselective anionic cyclisation with loss of aromaticity to give a bicyclic enone which may be converted in nine steps to (±)-kainic acid.",

author = "Jonathan Clayden and Kirill Tchabanenko",

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T1 - Synthesis of (±)-kainic acid by dearomatising cyclisation of a lithiated N-benzyl p-anisamide

AU - Clayden, Jonathan

AU - Tchabanenko, Kirill

PY - 2000/2/21

Y1 - 2000/2/21

N2 - N-Benzyl p-anisamide 6, on lithiation with Bu(t)Li in the presence of HMPA, undergoes a stereoselective anionic cyclisation with loss of aromaticity to give a bicyclic enone which may be converted in nine steps to (±)-kainic acid.

AB - N-Benzyl p-anisamide 6, on lithiation with Bu(t)Li in the presence of HMPA, undergoes a stereoselective anionic cyclisation with loss of aromaticity to give a bicyclic enone which may be converted in nine steps to (±)-kainic acid.

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U2 - 10.1039/A909325G

DO - 10.1039/A909325G

M3 - Article (Academic Journal)

AN - SCOPUS:0034696110

SN - 1359-7345

SP - 317

EP - 318

JO - Chemical Communications

JF - Chemical Communications

IS - 4

ER -

Synthesis of (±)-kainic acid by dearomatising cyclisation of a lithiated N-benzyl p-anisamide

Abstract

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