Ivorenolide B, an Immunosuppressive 17-Membered Macrolide from Khaya ivorensis: Structural Determination and Total Synthesis

被引：33

作者：

Wang, Yao ^{[1
]}

Liu, Qun-Fang ^{[2
]}

Xue, Ji-Jun ^{[1
]}

Zhou, Yu ^{[2
]}

Yu, Huang-Chao ^{[1
]}

Yang, Sheng-Ping ^{[2
]}

Zhang, Bo ^{[2
]}

Zuo, Jian-Ping ^{[2
]}

Li, Ying ^{[1
]}

Yue, Jian-Min ^{[1
,2
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 07期

基金：

中国国家自然科学基金;

关键词：

NATURAL-PRODUCTS;

D O I：

10.1021/ol500667d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ivorenolide B (1), an unprecedented 17-membered macrolide featuring conjugated acetylenic bonds and four chiral centers, was isolated from Khaya ivorensis. The structure of 1 was fully determined by spectroscopic analysis and total syntheses of its four most possible stereoisomers. Compound 1 showed significant immunosuppressive activity.

引用

收藏

页码：2062 / 2065

页数：4

相关论文

共 23 条

[1] LIMONOID CHEMISTRY OF GENUS KHAYA (MELIACEAE) [J].

ADESIDA, GA ;

STYLES, BT .

PHYTOCHEMISTRY, 1971, 10 (08) :1845-&

[2] Studies on the anti-inflammatory and toxic effects of the stem bark of Khaya ivorensis (Meliaceae) on rats [J].

Agbedahunsi, JM ;

Fakoya, FA ;

Adesanya, SA .

PHYTOMEDICINE, 2004, 11 (06) :504-508

[3] Reactivity and selectivity of 1,3-diyn-6-enes in electrophilic transition metal-catalyzed reactions [J].

Cho, Eun Jin ;

Kim, Mansuk ;

Lee, Daesung .

ORGANIC LETTERS, 2006, 8 (23) :5413-5416

[4] Total synthesis of (+)-brasilenyne. Application of an intramolecular silicon-assisted cross-coupling reaction [J].

Denmark, SE ;

Yang, SM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (39) :12432-12440

[5] Stereoselective synthesis of (3S,8R,9R,10R)-heptadeca-1-ene-4,6-diyne tetrol and its 3-epimer from D-mannitol [J].

Ghosh, Subhash ;

Pradhan, Tapan Kumar .

SYNLETT, 2007, (15) :2433-2435

[6] Macrocyclization by ring-closing metathesis in the total synthesis of natural products:: Reaction conditions and limitations [J].

Gradillas, Ana ;

Perez-Castells, Javier .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (37) :6086-6101

[7] Universal Peptidomimetics [J].

Ko, Eunhwa ;

Liu, Jing ;

Perez, Lisa M. ;

Lu, Genliang ;

Schaefer, Amber ;

Burgess, Kevin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (03) :462-477

[8] Total Syntheses of Isomeric Spiroacetal Marine Natural Products Attenols A and B [J].

Kumar, Vemula Praveen ;

Kavitha, Nerella ;

Chandrasekhar, Srivari .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (28) :6325-6334

[9] Weak Interactions Dominating the Supramolecular Self-Assembly in a Salt: A Designed Single-Crystal-to-Single-Crystal Topochemical Polymerization of a Terminal Aryldiacetylene [J].

Li, Zhong ;

Fowler, Frank W. ;

Lauher, Joseph W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (02) :634-643

[10] An Efficient Approach to Substituted 1,5,7,8,9-Pentahydrocyclopenta[h]-2-Benzopyran-3-one Derivatives by a Palladium-Catalyzed Tandem Reaction of 2,7-Alkadiynylic Carbonates with 2,3-Allenoic Acids [J].

Lian, Xiongdong ;

Ma, Shengming .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (43) :8255-8258