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A fast and straightforward route towards the synthesis of the lissoclimide class of anti-tumour agents |
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| Authors: | Tuan Minh Nguyen Jean-Jacques Youte Angie Cheong Benjamin SW Tan Mark S Butler |
| Institution: | a Institute of Chemical and Engineering Sciences (ICES), Agency for Science Technology and Research, 8 Biomedical Grove, #07-01/2/3, Neuros, Singapore 138665 b MerLion Pharmaceuticals Pte Ltd, 1 Science Park Road, #05-01 The Capricorn, Singapore Science Park II, Singapore 117528 c Department of Pharmacy, Faculty of Science, National University of Singapore, Singapore 117543 |
| 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. |
| Keywords: | Aldol reaction anti-Tumour agents Lissoclimides Natural products Terpenoids |
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