Enantiospecific synthesis of methyl ester side chain of bishomoharringtonine

被引：2

作者：

Sun, Moran ^{[1
]}

Gao, Kaige ^{[1
]}

Zheng, Jiaxin ^{[1
]}

Lai, Yaowen ^{[1
]}

Yang, Hua ^{[1
]}

机构：

[1] Zhengzhou Univ, Sch Pharmaceut Sci, Zhengzhou 450001, Peoples R China

来源：

RESEARCH ON CHEMICAL INTERMEDIATES | 2015年 / 41卷 / 02期

关键词：

Bishomoharringtonine; Enantiospecificity; Wittig reaction; 2,3]-Meisenheimer rearrangement; ALKALOIDS; HOMOHARRINGTONINE; HARRINGTONIA;

D O I：

10.1007/s11164-013-1263-4

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantiospecific total synthesis of methyl ester derivative of bishomoharringtonine side chain is accomplished from l-glutamate in 41 % overall yield. Key feature of the synthesis is the construction of the chiral quaternary center by a Wittig reaction to obtain single configuration trisubstitutes olefin and the subsequent complete chirality transfer of [2, 3]-Meisenheimer rearrangement.

引用

页码：1181 / 1190

页数：10

共 50 条

[31] SYNTHESIS OF SERINE METHYL ESTER HYDROCHLORIDE
PAKULA, R
MARJANKO.B
ACTA POLONIAE PHARMACEUTICA, 1970, 27 (05): : 517 - &
[32] Synthesis of (±)-Protoconstipatic acid methyl ester
Thavornyutikarn, Praput
Kongsak, Chawanakorn
Chailungka, Anurak
Rithchumpon, Puracheth
Junpirom, Thiti
Meepowpan, Puttinan
TETRAHEDRON, 2023, 145
[33] Total Synthesis of (±)-Pentalenolactone A Methyl Ester
Liu, Qi
Yue, Guozong
Wu, Na
Lin, Guang
Li, Yuanzhen
Quan, Junmin
Li, Chuang-chuang
Wang, Guoxin
Yang, Zhen
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (48) : 12072 - 12076
[34] Total synthesis of zincophorin methyl ester
Defosseux, M
Blanchard, N
Meyer, C
Cossy, J
ORGANIC LETTERS, 2003, 5 (22) : 4037 - 4040
[35] A TOTAL SYNTHESIS OF HERBOXIDIENE METHYL ESTER
Premraj, Rajaratnam
McLeod, Malcolm D.
Simpson, Gregory W.
Banwell, Martin G.
HETEROCYCLES, 2012, 85 (12) : 2949 - 2976
[36] Formal Synthesis of (±)-Pentalenolactone A Methyl Ester
Niu, Guang-Hao
Liu, Pin-Heng
Hung, Wei-Chun
Tseng, Ping-Yao
Chuang, Gary Jing
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (16): : 10172 - 10182
[37] Stereoselective synthesis of thailandamide A methyl ester
Sharma, Himangshu
Ganguly, Swapnamoy
Sahana, Moinul Haque
Goswami, Rajib Kumar
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (07) : 1409 - 1419
[38] Enhanced synthesis of branched-chain methyl ester sulfonates via surfactant-assisted sulfonation of methyl oleate
Attanatho, Lalita
Sisuthog, Wanchana
Butniam, Pathumrat
Thanmongkhon, Yoothana
Prasongthum, Natthawan
Khamdaeng, Punyaporn
Kongparakul, Suwadee
Suemanotham, Amornrat
BIOMASS CONVERSION AND BIOREFINERY, 2024,
[39] An Efficient Asymmetric Synthesis of the Mercaptopyrrolidine Side Chain of an Important a-Methyl Carbapenem Antibiotic
Tetrahedron Lett, 18 (3203):
[40] Weakening of a polyethylene chain by methyl side groups
Hageman, JCL
de Wijs, GA
de Groot, RA
Meier, RJ
SOFT MATERIALS, 2003, 1 (02) : 223 - 233

← 1 2 3 4 5 →