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

doi:10.1039/c3ob40480c

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

Department of Chemistry

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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 language	English
Pages (from-to)	3846-3854
Number of pages	9
Journal	Organic and Biomolecular Chemistry
Volume	11
Issue number	23
DOIs	https://doi.org/10.1039/c3ob40480c
State	Published - 2013

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10.1039/c3ob40480c

CCDC 912553: Experimental Crystal Structure Determination
Ramanathan, M. (Creator), Tan, C. (Creator), Chang, W. (Creator), Tsai, H. (Creator) & Hou, D. (Creator), The Cambridge Structural Database, 2013
DOI: 10.5517/cczml6c, http://www.ccdc.cam.ac.uk/services/structure_request%3Fid=doi:10.5517/cczml6c&sid=DataCite
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title = "Synthesis of the decalin core of codinaeopsin via an intramolecular Diels-Alder reaction",

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.",

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T1 - Synthesis of the decalin core of codinaeopsin via an intramolecular Diels-Alder reaction

AU - Ramanathan, Mani

AU - Tan, Chun Jui

AU - Chang, Wen Jung

AU - Tsai, Hui Hsu Gavin

AU - Hou, Duen Ren

PY - 2013

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N2 - 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.

AB - 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.

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U2 - 10.1039/c3ob40480c

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EP - 3854

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 23

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

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CCDC 912553: Experimental Crystal Structure Determination

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