A concise synthesis of the dihydroxy styryllactone, 7-epi-goniodiol

被引：2

作者：

Zeng, PingLi ^{[1
]}

Wang, Dong ^{[2
]}

Zhou, Junhui ^{[1
]}

Dong, Zhibing ^{[3
]}

机构：

[1] Zhejiang Pharmaceut Coll, Sch Biol & Pharmaceut, Ningbo 315100, Zhejiang, Peoples R China

[2] Zhejiang Pharmaceut Coll, Practice & Training Ctr, Ningbo 315100, Zhejiang, Peoples R China

[3] Wuhan Inst Technol, Sch Chem & Environm Engn, Wuhan 430073, Peoples R China

来源：

JOURNAL OF CHEMICAL RESEARCH | 2016年 / 06期

基金：

中国国家自然科学基金;

关键词：

synthesis; styryllactone; 7-epi-goniodiol; goniodiol; STYRYL LACTONES; GONIOTHALAMUS; OXIDATION; ALCOHOLS;

D O I：

10.3184/174751916X14615896825798

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A short and efficient stereoselective synthesis of dihydroxy styryllactone 7-epi-goniodiol has been achieved in nine steps and 20% overall yield, starting from readily available L-erythrose monoacetonide. The key steps of the synthesis involved a stereocontrolled Grignard reaction, a Stille-Gennari reaction and a one-pot acetonide deprotection-lactonisation.

引用

页码：331 / 334

页数：4

共 50 条

[31] Concise Synthesis of 7-Deoxypsammaplysins K and O and 7-Deoxyceratinamide A by 1,3-Dipole Cycloaddition [J].

Zhang, Lijie ;

Wang, Rongya ;

Wang, Chao ;

Liu, Bingyan ;

Yang, Jinfeng ;

Zhang, Zhongchao ;

Huang, Jun ;

Yang, Zhen .

ORGANIC LETTERS, 2022, 24 (21) :3786-3791

[32] Stereoselective total synthesis of bioactive styryllactones:: 9-deoxygoniopypyrone, goniopypyrone and 7-epi-goniofufurone [J].

Prasad, Kavirayani R. ;

Dhaware, Madhuri G. .

SYNTHESIS-STUTTGART, 2007, (23) :3697-3705

[33] CONCISE SYNTHESIS AND CELLULAR EVALUATION OF 3′-FORMYL-4′, 6′-DIHYDROXY-2′-METHOXY-5′-METHYLCHALCONE (FMC) AND ITS ANALOGUES [J].

Xiang Zhuo ;

Li En-Zhen ;

Liang Hai ;

Guo Hong-Ju ;

Shi Ning ;

Zhang Xue-Hui ;

Qian Qi-Fang ;

Wu Jiu-Hong .

SYNTHETIC COMMUNICATIONS, 2014, 44 (21) :3139-3147

[34] Synthesis of 7,8-dihydroxy-5-hydroxymethyl-2-phenyl-chroman-4-one; the aglycon of actinoflavoside [J].

Suzuki, K ;

Tsuruga, T ;

Hiranuma, K ;

Yamaura, M .

SYNLETT, 2004, (01) :116-118

[35] Co(III)(salen)-catalyzed HKR of two stereocentered alkoxy- and azido epoxides: a concise enantioselective synthesis of (S,S)-reboxetine and (+)-epi-cytoxazone [J].

Reddy, R. Santhosh ;

Chouthaiwale, Pandurang V. ;

Suryavanshi, Gurunath ;

Chavan, Vilas B. ;

Sudalai, Arumugam .

CHEMICAL COMMUNICATIONS, 2010, 46 (27) :5012-5014

[36] Synthesis and characterization of 2, 7-dibromospiro [fluorene-9, 9'-(2', 7'-dihydroxy-1', 8'-disulfonic-xanthene)] [J].

Wang L.-Y. ;

Song Y.-J. ;

Cao D.-R. .

Huanan Ligong Daxue Xuebao/Journal of South China University of Technology (Natural Science), 2010, 38 (09) :75-79

[37] Design, synthesis and in vitro antitumour activity of new goniofufurone and 7-epi-goniofufurone mimics with halogen or azido groups at the C-7 position [J].

Francuz, Jovana ;

Kovacevic, Ivana ;

Popsavin, Mirjana ;

Benedekovic, Goran ;

Sreco Zelenovic, Bojana ;

Kojic, Vesna ;

Jakimov, Dimitar ;

Aleksic, Lidija ;

Bogdanovic, Gordana ;

Srdic-Rajic, Tatjana ;

Loncar, Eva ;

Rodic, Marko V. ;

Divjakovic, Vladimir ;

Popsavin, Velimir .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 128 :13-24

[38] Novel O-methyl goniofufurone and 7-epi-goniofufurone derivatives: synthesis, in vitro cytotoxicity and SAR analysis [J].

Francuz, Jovana ;

Popsavin, Mirjana ;

Djokic, Sanja ;

Kojic, Vesna ;

Srdic-Rajic, Tatjana ;

Rodic, Marko V. ;

Jakimov, Dimitar ;

Popsavin, Velimir .

MEDCHEMCOMM, 2018, 9 (12) :2017-2027

[39] SYNTHESIS, MOLECULAR DOCKING, MOLECULAR PROPERTIES ESTIMATIONS AND ANTIINFLAMATORY ACTIVITY OF 5, 7-DIHYDROXY-3' PRENYL FLAVANONE [J].

Krishna, Badikela Rama ;

Ch, Rathnakar ;

Kemisetti, Durgaprasad ;

Surendran, Vijayaraj ;

Ravula, Parameshwar .

HETEROCYCLIC LETTERS, 2022, 12 (04) :797-804

[40] Study on synthesis of key squalamine intermediate 7α, 24R-dihydroxy-5α-cholestan-3-one [J].

Zhou, Shuai ;

Zheng, Yang ;

Yang, Beibei ;

Zhong, Jiawei ;

Shi, Haijian .

STEROIDS, 2019, 151

← 1 2 3 4 5 →