A fast and straightforward route towards the synthesis of the lissoclimide class of anti-tumour agents

Nguyen, Tuan Minh, Vu, Nguyen Quang, Youte, Jean-Jacques, Lau, Jacelyn, Chong, Angie, Ho, Ying San, Tan, Benjamin S. W., Yoganathan. K., Butler, Mark S. and Chai, Christina L. L. (2010) A fast and straightforward route towards the synthesis of the lissoclimide class of anti-tumour agents. Tetrahedron, 66 47: 9270-9276. doi:10.1016/j.tet.2010.09.031


Author Nguyen, Tuan Minh
Vu, Nguyen Quang
Youte, Jean-Jacques
Lau, Jacelyn
Chong, Angie
Ho, Ying San
Tan, Benjamin S. W.
Yoganathan. K.
Butler, Mark S.
Chai, Christina L. L.
Title A fast and straightforward route towards the synthesis of the lissoclimide class of anti-tumour agents
Journal name Tetrahedron   Check publisher's open access policy
ISSN 0040-4020
1464-5416
Publication date 2010-11-20
Sub-type Article (original research)
DOI 10.1016/j.tet.2010.09.031
Volume 66
Issue 47
Start page 9270
End page 9276
Total pages 7
Place of publication Kidlington, Oxford, United Kingdom
Publisher Pergamon
Language eng
Abstract The synthesis of the chiral core structure of the lissoclimide class of anti-tumour agents containing three rings, including a chiral succinimide subunit and an exocyclic double bond, has been investigated. The compound 7 was obtained, without the use of any protecting groups for the alcohol at C-12, via an asymmetric boron-mediated aldol addition as the key step to install the chiral centres of the rare succinimido methanol moiety. This was followed by a sequence of lactonisation, microwave-assisted amidation and imidation reactions.
Keyword Aldol reaction
Anti-Tumour agents
Lissoclimides
Natural products
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: Institute for Molecular Bioscience - Publications
 
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Created: Fri, 30 Sep 2011, 16:51:15 EST by Mark Butler on behalf of Institute for Molecular Bioscience