SYNTHESIS OF BOTH ENANTIOMERS OF PROTOBERBERINES VIA LATERALLY LITHIATED (S)-4-ISOPROPYL-2-(o-TOLYL)-OXAZOLINES

Tsutomu Fukuda; Masatomo Iwao

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SYNTHESIS OF BOTH ENANTIOMERS OF PROTOBERBERINES VIA LATERALLY LITHIATED (S)-4-ISOPROPYL-2-(o-TOLYL)-OXAZOLINES

机译：通过横向锂化的（S）-4-异丙烯基-2-（邻甲苯基）-恶唑啉合成小BER碱中的两种对映体

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The addition of the laterally lithiated (S)-4-isopropyl-2-(o-tolyl)oxazoline (1) to 6,7-dimethoxy-3,4-dihydroisoquinoline (2) proceeded in modest diastereoselectivity.However,the addition products (3a) and (3b) were easily separated by column chromatography over silica gel.Acid-catalyzed lactamization of 3a and 3b followed by LiAlH4-reduction afforded the corresponding optically pure protoberberines (8a) and (8b),respectively.This procedure was successfully applied to the synthesis of both enantiomers of xylopinine and bharatamine.

机译：将侧向锂化的（S）-4-异丙基-2-（邻甲苯基）恶唑啉（1）添加到6,7-二甲氧基-3,4-二氢异喹啉（2）中的非对映选择性很适度。（3a）和（3b）易于通过硅胶柱色谱分离.3a和3b的酸催化内酰胺化反应，再用LiAlH4还原，分别得到相应的光学纯原小ber碱（8a）和（8b）。应用于合成木糖嘌呤和巴拉丹明的对映体。

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《Heterocycles: An International Journal for Reviews and Communications in Heterocyclic Chemistry》 |2007年第0期|共20页
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Tsutomu Fukuda; Masatomo Iwao;
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1. SYNTHESIS OF BOTH ENANTIOMERS OF PROTOBERBERINES VIA LATERALLY LITHIATED (S)-4-ISOPROPYL-2-(o-TOLYL)-OXAZOLINES [J] . Tsutomu Fukuda, Masatomo Iwao Heterocycles: An International Journal for Reviews and Communications in Heterocyclic Chemistry . 2007,第0期

机译：通过横向锂化的（S）-4-异丙烯基-2-（邻甲苯基）-恶唑啉合成小BER碱中的两种对映体
2. Synthesis of 3-substituted 8-hydroxy-3,4-dihydroisocoumarins via successive lateral and ortho-lithiations of 4,4-dimethyl-2-(O-tolyl)oxazoline [J] . Naruki Tahara, Tsutomu Fukuda, Masatomo Iwao Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2004,第26期

机译：通过4,4-二甲基-2-（O-甲苯基）恶唑啉的连续侧向和邻位锂化反应合成3-取代的8-羟基-3,4-二氢异香豆素
3. Synthesis of 3-substituted 8-hydroxy-3,4-dihydroisocoumarins via successive lateral and ortho-lithiations of 4,4-dimethyl-2-(o-tolyl)oxazoline [J] . Tahara N, Fukuda T, Iwao M Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2004,第26期

机译：通过4,4-二甲基-2-（邻甲苯基）恶唑啉的连续侧向和邻位锂化反应合成3-取代的8-羟基-3,4-二氢异香豆素
4. Synthesis and properties of thermo-responsive tooth-brush likecopolymer consisted of PNIPAM and chiral-oxazoline side-chain [C] . Haruka Takebuchi, Ren-Hua Jin 日本化学会春季年会 . 2020

机译：热响应齿刷基金聚合物的合成与性质由肺脂和氧氮杂侧链组成
5. Part I. The enantiospecific total synthesis of tryprostatin A and B as well as their enantiomers and mismatched pairs. Part II. The enantiospecific, stereospecific total synthesis of the ring-A oxygenated sarpagine indole alkaloids (+)-majvinine, (+)-10-methoxyaffinisine and (+)-N(a)-methylsarpagine as well as the first total synthesis of the Alstonia bisindole alkaloid macralstonidine [D] . Zhao, Shuo 2007

机译：第一部分。Tryprostatin A和B及其对映异构体和错配对的对映体特异性合成。第二部分对映体，立体有择的环A氧化的沙鲁帕辛吲哚生物碱（+）-majvinine，（+）-10-甲氧基affinisine和（+）-N（a）-甲基sarpagine的全合成以及Alstonia bisindole的第一个全合成生物碱Macralstonidine
6. Synthesis and structure−activity relationship of 8-substituted protoberberine derivatives as a novel class of antitubercular agents [O] . Ying-Hong Li, Hai-Gen Fu, Feng Su, 2013

机译：一类新型抗结核药8-取代的原小to碱衍生物的合成及其构效关系
7. Asymmetric synthesis of 3-substituted 3,4-dihydroisocoumarins via stereoselective addition of laterally lithiated chiral 2-(-tolyl)oxazolines to aldehydes followed by diastereomer-selective lactonization [O] . Kurosaki Yuji, Fukuda Tsutomu, Iwao Masatomo 2005

机译：通过立体选择性地将侧链锂化的手性2 - （ - 甲苯基）恶唑啉加成醛，然后进行非对映体选择性内酯化，不对称合成3-取代的3,4-二氢异香豆素

SYNTHESIS OF BOTH ENANTIOMERS OF PROTOBERBERINES VIA LATERALLY LITHIATED (S)-4-ISOPROPYL-2-(o-TOLYL)-OXAZOLINES

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