A Concise Synthesis of Presilphiperfolane Core through a Tandem TMTU-Co-Catalyzed Pauson-Khand Reaction and a 6π Electrocyclization Reaction (TMTU=Tetramethyl Thiourea)

被引：21

作者：

Zhang, Zichun ^{[1
]}

Li, Yuanhe ^{[2
,3
]}

Zhao, Dandan ^{[1
,2
,3
]}

He, Yingdong ^{[1
]}

Gong, Jianxian ^{[1
]}

Yang, Zhen ^{[1
]}

机构：

[1] Peking Univ Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen 518055, Peoples R China

[2] Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China

[3] Beijing Natl Lab Mol Sci, Coll Chem & Mol Engn, Key Lab Bioorgan Chem & Mol Engn Minist Educ, Beijing 100871, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 06期

基金：

美国国家科学基金会;

关键词：

electrocyclic reactions; tandem reaction; Pauson-Khand reaction; presilphiperfolane core; total synthesis; OCCURRING TERPENE DERIVATIVES; ENDIANDRIC ACID CASCADE; STEREOCONTROLLED TOTAL-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ORGANIC-SYNTHESIS; ESSENTIAL OIL; BIOMIMETIC APPROACH; ENZYMATIC FORMATION; SESQUITERPENES; STEREOCHEMISTRY;

D O I：

10.1002/chem.201605438

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of strained polycyclic systems from readily available precursors with a minimum number of steps and with regio-and stereochemical control constitutes an important synthetic challenge. Herein, we report a tandem reaction comprising Co-TMTU (tetramethyl thiourea)-catalyzed Pauson-Khand (PK) and 6pelectrocyclization reactions for the formation of the highly strained core of presilphiperfolanols. The developed chemistry has been applied to the total syntheses of 4epi- presilphiperfolan-8-ol and 7-epi-presilphiperfolan-1-ol.

引用

页码：1258 / 1262

页数：5

共 6 条

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Tang, YF
Deng, LJ
Zhang, YD
Dong, GB
Chen, JH
Yang, Z
ORGANIC LETTERS, 2005, 7 (04) : 593 - 595
[2] Co-catalyzed tandem Pauson-Khand type reaction/dimerization of terminal diynes in the presence of cyclopentadiene under CO pressure
Do, Han Kim
Young, Keun Chung
Jin, Wook Han
Bulletin of the Korean Chemical Society, 2007, 28 (07) : 1089 - 1090
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Kim, Do Han
Chung, Young Kenn
Han, Jin Wook
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2007, 28 (07): : 1089 - 1090
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Tang, YF
Zhang, YD
Dai, MJ
Luo, TP
Deng, LJ
Chen, JH
Yang, Z
ORGANIC LETTERS, 2005, 7 (05) : 885 - 888
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Jiao, Lei
Lin, Mu
Zhuo, Lian-Gang
Yu, Zhi-Xiang
ORGANIC LETTERS, 2010, 12 (11) : 2528 - 2531
[6] New reactivity of (RCCCH2OH)Co2(CO)6 complexes in the Pauson-Khand reaction in the presence of CF3COOH:: synthesis of methyl substituted cyclopentenones
Periasamy, M
Lakshmi, M
Rao, N
Rajesh, T
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 571 (02) : 183 - 187

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