Abstract
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.
Original language | English |
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Pages (from-to) | 3846-3854 |
Number of pages | 9 |
Journal | Organic and Biomolecular Chemistry |
Volume | 11 |
Issue number | 23 |
DOIs | |
State | Published - 2013 |
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CCDC 912553: Experimental Crystal Structure Determination
Tsai, H. (Contributor), Hou, D. (Contributor), Chang, W. (Contributor), Tan, C. (Contributor) & Ramanathan, M. (Contributor), The Cambridge Structural Database, 1 Jan 2013
DOI: 10.5517/cczml6c, https://doi.org/10.5517%2Fcczml6c
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