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Jongcharoenkamol J, Chuathong P, Amako Y, et al. Selective Divergent Synthesis of Indanols, Indanones, and Indenes via Acid-Mediated Cyclization of ( Z)- and ( E)-(2-Stilbenyl)methanols and Its Application for the Synthesis of Paucifloral F Derivatives. J Org Chem. 2018;83(21):13184-13210doi: 10.1021/acs.joc.8b01921.
Jongcharoenkamol, J., Chuathong, P., Amako, Y., Kono, M., Poonswat, K., Ruchirawat, S., & Ploypradith, P. (2018). Selective Divergent Synthesis of Indanols, Indanones, and Indenes via Acid-Mediated Cyclization of ( Z)- and ( E)-(2-Stilbenyl)methanols and Its Application for the Synthesis of Paucifloral F Derivatives. The Journal of organic chemistry, 83(21), 13184-13210. https://doi.org/10.1021/acs.joc.8b01921
Jongcharoenkamol, Jira, et al. "Selective Divergent Synthesis of Indanols, Indanones, and Indenes via Acid-Mediated Cyclization of ( Z)- and ( E)-(2-Stilbenyl)methanols and Its Application for the Synthesis of Paucifloral F Derivatives." The Journal of organic chemistry vol. 83,21 (2018): 13184-13210. doi: https://doi.org/10.1021/acs.joc.8b01921
Jongcharoenkamol J, Chuathong P, Amako Y, Kono M, Poonswat K, Ruchirawat S, Ploypradith P. Selective Divergent Synthesis of Indanols, Indanones, and Indenes via Acid-Mediated Cyclization of ( Z)- and ( E)-(2-Stilbenyl)methanols and Its Application for the Synthesis of Paucifloral F Derivatives. J Org Chem. 2018 Nov 02;83(21):13184-13210. doi: 10.1021/acs.joc.8b01921. Epub 2018 Oct 22. PMID: 30346169.
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J Org Chem. 2018 Nov 02;83(21):13184-13210. doi: 10.1021/acs.joc.8b01921. Epub 2018 Oct 22.

Selective Divergent Synthesis of Indanols, Indanones, and Indenes via Acid-Mediated Cyclization of ( Z)- and ( E)-(2-Stilbenyl)methanols and Its Application for the Synthesis of Paucifloral F Derivatives.

The Journal of organic chemistry

Jira Jongcharoenkamol, Patsapon Chuathong, Yuka Amako, Masato Kono, Kasam Poonswat, Somsak Ruchirawat, Poonsakdi Ploypradith

Affiliations

  1. Program in Chemical Biology , Chulabhorn Graduate Institute, Chulabhorn Royal Academy , 54 Kamphaeng Phet 6 Road , Laksi, Bangkok 10210 , Thailand.
  2. Laboratory of Medicinal Chemistry , Chulabhorn Research Institute , 54 Kamphaeng Phet 6 Road , Laksi, Bangkok 10210 , Thailand.
  3. Centre of Excellence on Environmental Health and Toxicology, Commission on Higher Education (CHE), Ministry of Education , 54 Kamphaeng Phet 6 Road , Laksi, Bangkok 10210 , Thailand.

PMID: 30346169 DOI: 10.1021/acs.joc.8b01921

Abstract

Starting from bromo/iodobenzaldehyde derivatives, the corresponding ( Z)- and ( E)-(2-stilbenyl)methanols could be prepared in 2-5 steps via Pd-catalyzed cross-coupling reactions (Sonogashira and Heck reactions) followed by aryllithium/aryl Grignard addition. For the ( E)-stilbenes, subsequent acid-mediated cyclization using p-TsOH immobilized on silica (PTS-Si) at low temperatures furnished the 2,3- trans-1-indanols with complete stereocontrol at the C2-C3. Further oxidization of the alcohol provided the indanones, which are structurally related to the natural product paucifloral F. At higher temperatures, 1,2- and 2,3-disubstituted indenes could be selectively prepared in good to excellent yields. On the other hand, the ( Z)-stilbenes, under similar conditions (PTS-Si), did not give the indanols; only the 1,2-disubstituted indenes could be obtained. To gain further insights into the stereochemistry at C2-C3 for the ( Z)-stilbenes, hydride or azide was employed as a nucleophile; the corresponding indane products were obtained with the cis stereochemistry at the C2-C3. Thus, the ( Z)- or ( E)-olefin geometry of the substrate directed the stereoselective indanyl cyclization to furnish the cis or trans at the C2-C3 ring junction, respectively, while reaction conditions controlled the selectivity of the product types.

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