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Molecules 2018, 23(2), 255; doi:10.3390/molecules23020255

Novel Topologically Complex Scaffold Derived from Alkaloid Haemanthamine

1
Department of Chemistry and Biochemistry, Texas State University, San Marcos, TX 78666, USA
2
Dipartimento di Scienze Chimiche, Università di Napoli Federico II, Complesso Universitario Monte Sant’Angelo, Via Cintia 4, 80126 Napoli, Italy
3
Department of Pharmacotherapy and Pharmaceutics, Faculté de Pharmacie, Université Libre de Bruxelles (ULB), 1050 Brussels, Belgium
*
Authors to whom correspondence should be addressed.
Received: 8 January 2018 / Revised: 24 January 2018 / Accepted: 25 January 2018 / Published: 28 January 2018
(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products 2018)
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Abstract

The generation of natural product-like compound collections has become an important area of research due to low hit rates found with synthetic high-throughput libraries. One method of generating compounds occupying the areas of chemical space not accessible to synthetic planar heterocyclic structures is the utilization of natural products as starting materials. In the current work, using a ring-closing iodoalkoxylation reaction, alkaloid haemanthamine was transformed into a unique structural framework possessing an intricate ring system and a large number of stereocenters. The structure of the new compound was confirmed with an X-ray analysis. A small number of derivatives of this new compound were synthesized as a demonstration of the possibility of generating a large natural product-like compound collection based on the new structural framework. View Full-Text
Keywords: natural product-like; diversity-oriented synthesis; haemanthamine; haemanthidine; iodoalkoxylation; biological activity natural product-like; diversity-oriented synthesis; haemanthamine; haemanthidine; iodoalkoxylation; biological activity
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MDPI and ACS Style

Govindaraju, K.; Masi, M.; Colin, M.; Mathieu, V.; Evidente, A.; Hudnall, T.W.; Kornienko, A. Novel Topologically Complex Scaffold Derived from Alkaloid Haemanthamine. Molecules 2018, 23, 255.

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