Stereo selective synthesis of C3-C12 fragment of iriomoteolide-1a

被引：1

作者：

Sharma, Gangavaram V. M. ^{[1
]}

Rajender, Karnekanti ^{[1
,2
]}

机构：

[1] Indian Inst Chem Technol, CSIR, Organ & Biomol Chem Div, Hyderabad 500007, Andhra Prades, India

[2] Govt Polytech, Warangal 506007, Telangana State, India

来源：

JOURNAL OF SAUDI CHEMICAL SOCIETY | 2018年 / 22卷 / 02期

关键词：

Iriomoteolide-1a; Mannich reaction; Sharpless epoxidation; Keck allylation; Cross-metathesis; DINOFLAGELLATE AMPHIDINIUM-SP; OLEFIN METATHESIS; STEREOSELECTIVE-SYNTHESIS; MARINE; MACROLIDES; DINOPHYCEAE; ALLYLATION; ALDEHYDE;

D O I：

10.1016/j.jscs.2016.01.008

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convergent and flexible synthetic route for the synthesis of C3-C12 fragment of iriomoteolide-1a is described. The key steps are: Mannich reaction, Keck asymmetric allylation, Sharpless asymmetric epoxidation and cross-metathesis protocol. (C) 2016 King Saud University. Production and hosting by Elsevier B.V.

引用

页码：165 / 172

页数：8

共 36 条

[1] Marine natural products
Blunt, John W.
Copp, Brent R.
Hu, Wan-Ping
Munro, Murray H. G.
Northcote, Peter T.
Prinsep, Michele R.
[J]. NATURAL PRODUCT REPORTS, 2007, 24 (01) : 31 - 86
[2] Synthesis of Iriomoteolide-1a C13-C23 Fragment via Asymmetric Conjugate Addition and Julia-Kocienski Coupling Reaction
Chin, Yen-Jin
Wang, Shun-Yi
Loh, Teck-Peng
[J]. ORGANIC LETTERS, 2009, 11 (16) : 3674 - 3676
[3] Synthesis of the C1-C12 Fragment of iriomoteolide 1a by Sequential Catalytic Asymmetric Vinylogous Aldol Reactions
Fang, Lijing
Xue, Haoran
Yang, Jiong
[J]. ORGANIC LETTERS, 2008, 10 (20) : 4645 - 4648
[4] Enantioselective Synthesis of a Diastereomer of Iriomoteolide-1a. What Is the Correct Structure of the Natural Product?
Fang, Lijing
Yang, Jiong
Yang, Fei
[J]. ORGANIC LETTERS, 2010, 12 (14) : 3124 - 3127
[5] A highly stereoselective asymmetric synthesis of (-)-lobeline and (-)-sedamine
Felpin, FX
Lebreton, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (26) : 9192 - 9199
[6] An efficient organocatalytic route to the atorvastatin side-chain
George, Shyla
Sudalai, Arumugam
[J]. TETRAHEDRON LETTERS, 2007, 48 (48) : 8544 - 8546
[7] Enantioselective Syntheses of the Proposed Structures of Cytotoxic Macrolides Iriomoteolide-1a and-1b
Ghosh, Arun K.
Yuan, Hao
[J]. ORGANIC LETTERS, 2010, 12 (14) : 3120 - 3123
[8] Stereoselective synthesis of the C1-C12 segment of iriomoteolide-1a: a very potent macrolide antitumor agent
Ghosh, Arun K.
Yuan, Hao
[J]. TETRAHEDRON LETTERS, 2009, 50 (13) : 1416 - 1418
[9] Gogoi N, 2006, EUR J ORG CHEM, V2006, P1722, DOI [10.1002/ejoc.200500833, 10.1002/ejoe.200500833]
[10] Recent advances in olefin metathesis and its application in organic synthesis
Grubbs, RH
Chang, S
[J]. TETRAHEDRON, 1998, 54 (18) : 4413 - 4450

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