摘要
We describe the synthesis of the decalin core of codinaeopsin (1), a tryptophan-polyketide hybrid natural product with promising antimalarial activity (IC50 4.7 μM, against Plasmodium falciparum), via an intramolecular Diels-Alder (IMDA) reaction. A convergent synthesis was developed to prepare the precursors for the IMDA reaction in 10 steps. The exo cycloadducts were derived from thermal, IMDA reactions of the substrates containing a Weinreb amide or ester conjugated dienophile, and the endo adducts were from Lewis acid promoted reactions of the substrates with a formyl group. Both exo and endo products of the IMDA were exclusively isolated and characterized by NMR spectroscopy. One endo cycloadduct was further confirmed with X-ray crystallography. Theoretical calculations reveal the influence of the substituents of the decalin core on the IMDA process.
原文 | ???core.languages.en_GB??? |
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頁(從 - 到) | 3846-3854 |
頁數 | 9 |
期刊 | Organic and Biomolecular Chemistry |
卷 | 11 |
發行號 | 23 |
DOIs | |
出版狀態 | 已出版 - 2013 |
指紋
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CCDC 912553: Experimental Crystal Structure Determination
Ramanathan, M. (???dataset.roles.dataset.creator???), Tan, C.-J. (???dataset.roles.dataset.creator???), Chang, W.-J. (???dataset.roles.dataset.creator???), Tsai, H.-H. G. (???dataset.roles.dataset.creator???) & Hou, D.-R. (???dataset.roles.dataset.creator???), The Cambridge Structural Database, 2013
DOI: 10.5517/cczml6c, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cczml6c&sid=DataCite
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