Synthesis of the decalin core of codinaeopsin via an intramolecular Diels-Alder reaction

Mani Ramanathan, Chun Jui Tan, Wen Jung Chang, Hui Hsu Gavin Tsai, Duen Ren Hou

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8 Scopus citations

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 languageEnglish
Pages (from-to)3846-3854
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume11
Issue number23
DOIs
StatePublished - 2013

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