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.
|頁（從 - 到）||3846-3854|
|期刊||Organic and Biomolecular Chemistry|
|出版狀態||已出版 - 2013|
指紋深入研究「Synthesis of the decalin core of codinaeopsin via an intramolecular Diels-Alder reaction」主題。共同形成了獨特的指紋。
CCDC 912553: Experimental Crystal Structure Determination
Ramanathan, M. (???dataset.roles.dataset.creator???), Tan, C. (???dataset.roles.dataset.creator???), Chang, W. (???dataset.roles.dataset.creator???), Tsai, H. (???dataset.roles.dataset.creator???) & Hou, D. (???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