Approach to cis-Phlegmarine Alkaloids via Stereodivergent Reduction: Total Synthesis of (+)-Serratezomine E and Putative Structure of (−)-Huperzine N

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Título:	Approach to cis-Phlegmarine Alkaloids via Stereodivergent Reduction: Total Synthesis of (+)-Serratezomine E and Putative Structure of (−)-Huperzine N
Autor/a:	Bosch, Caroline; Fiser, Bela; Gómez-Bengoa, Enrique; Bradshaw, Ben; Bonjoch i Sesé, Josep
Otros autores:	Universitat de Barcelona
Abstract:	A unified strategy for the synthesis of the cisphlegmarine group of alkaloids is presented, leading to the first synthesis of serratezomine E (1) as well as the putative structure of huperzine N (2). A contrasteric hydrogenation method was developed based on the use of Wilkinson's catalyst, which allowed the facial selectivity of standard hydrogenation to be completely overturned. Calculations were performed to determine the mechanism, and structures for huperzines M and N are reassigned.
Materia(s):	-Alcaloides -Compostos heterocíclics -Síntesi orgànica -Productes naturals -Alkaloids -Heterocyclic compounds -Organic synthesis -Natural products
Derechos:	(c) American Chemical Society , 2015
Tipo de documento:	Artículo Artículo - Versión aceptada
Editor:	American Chemical Society
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Bosch, Caroline; Fiser, Bela; Gómez-Bengoa, Enrique; Bradshaw, Ben; Bonjoch i Sesé, Josep

Parra Montes, Claudio; Bosch, Caroline; Gómez-Bengoa, Enrique; Bonjoch i Sesé, Josep; Bradshaw, Ben

Bosch, Caroline; López-Lledó, Pablo; Bonjoch i Sesé, Josep; Bradshaw, Ben; Nieuwland, Pieter J.; Blanco-Ania, Daniel; Rutjes, Floris P. J. T.

Saborit Villarroya, Gisela; Bosch, Caroline; Parella, Teodor; Bradshaw, Ben; Bonjoch i Sesé, Josep

Saborit Villarroya, Gisela; Bosch, Caroline; Parella, Teodor; Bradshaw, Ben; Bonjoch i Sesé, Josep

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