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Organocatalytic enantioselective total synthesis of (-)-arboricine.
Org Lett. 2009 Jun 18; 11(12):2579-81.OL

Abstract

The tetracyclic indole alkaloid (-)-arboricine has been prepared using an asymmetric organocatalytic Pictet-Spengler reaction as the key step followed by a diastereoselective Pd-catalyzed iodoalkene/enolate cyclization. The absolute stereochemistry was unequivocally proven by X-ray crystallographic analysis and appeared to be opposite to the published structure in the original paper.

Authors+Show Affiliations

Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS, Amsterdam, The Netherlands.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

19514792

Citation

Wanner, Martin J., et al. "Organocatalytic Enantioselective Total Synthesis of (-)-arboricine." Organic Letters, vol. 11, no. 12, 2009, pp. 2579-81.
Wanner MJ, Boots RN, Eradus B, et al. Organocatalytic enantioselective total synthesis of (-)-arboricine. Org Lett. 2009;11(12):2579-81.
Wanner, M. J., Boots, R. N., Eradus, B., de Gelder, R., van Maarseveen, J. H., & Hiemstra, H. (2009). Organocatalytic enantioselective total synthesis of (-)-arboricine. Organic Letters, 11(12), 2579-81. https://doi.org/10.1021/ol900888e
Wanner MJ, et al. Organocatalytic Enantioselective Total Synthesis of (-)-arboricine. Org Lett. 2009 Jun 18;11(12):2579-81. PubMed PMID: 19514792.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Organocatalytic enantioselective total synthesis of (-)-arboricine. AU - Wanner,Martin J, AU - Boots,Rowan N A, AU - Eradus,Bram, AU - de Gelder,René, AU - van Maarseveen,Jan H, AU - Hiemstra,Henk, PY - 2009/6/12/entrez PY - 2009/6/12/pubmed PY - 2009/10/7/medline SP - 2579 EP - 81 JF - Organic letters JO - Org Lett VL - 11 IS - 12 N2 - The tetracyclic indole alkaloid (-)-arboricine has been prepared using an asymmetric organocatalytic Pictet-Spengler reaction as the key step followed by a diastereoselective Pd-catalyzed iodoalkene/enolate cyclization. The absolute stereochemistry was unequivocally proven by X-ray crystallographic analysis and appeared to be opposite to the published structure in the original paper. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19514792/Organocatalytic_enantioselective_total_synthesis_of_____arboricine_ L2 - https://doi.org/10.1021/ol900888e DB - PRIME DP - Unbound Medicine ER -