Total Synthesis of Enantiopure Chabrolonaphthoquinone B Via a Stereoselective Julia-Kocienski Olefination

被引：3
|
作者：
Rizos, Stergios R. [1 ]
Peitsinis, Zisis, V [1 ]
Koumbis, Alexandros E. [1 ]
机构：
[1] Aristotle Univ Thessaloniki, Dept Chem, Lab Organ Chem, Thessaloniki 54124, Greece
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 15期
关键词：
ENANTIOSELECTIVE SYNTHESIS; ACID; DERIVATIVES; METABOLITES; CONVENIENT; FRAGMENT;
D O I：
10.1021/acs.joc.1c01106
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The total synthesis of cytotoxic meroditerpenoid naphthoquinone derivative chabrolonaphthoquinone B (1) in an enantiospecific manner is divulged using a chiral pool approach. The key step of our synthetic route is a modified Julia olefination between a sulfone-bearing aliphatic fragment and a Diels-Alder-derived aromatic aldehyde, leading to the stereoselective construction of the E-trisubstituted double bond.
引用
收藏
页码：10440 / 10454
页数：15
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