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

All of RECERCAT

To access the full text documents, please follow this link: http://hdl.handle.net/2445/128419

Title:	Approach to cis-Phlegmarine Alkaloids via Stereodivergent Reduction: Total Synthesis of (+)-Serratezomine E and Putative Structure of (−)-Huperzine N
Author:	Bosch, Caroline; Fiser, Bela; Gómez-Bengoa, Enrique; Bradshaw, Ben; Bonjoch i Sesé, Josep
Other authors:	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.
Subject(s):	-Alcaloides -Compostos heterocíclics -Síntesi orgànica -Productes naturals -Alkaloids -Heterocyclic compounds -Organic synthesis -Natural products
Rights:	(c) American Chemical Society , 2015
Document type:	Article Article - Accepted version
Published by:	American Chemical Society
Share: