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

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dc.contributor	Universitat de Barcelona
dc.contributor.author	Bosch, Caroline
dc.contributor.author	Fiser, Bela
dc.contributor.author	Gómez-Bengoa, Enrique
dc.contributor.author	Bradshaw, Ben
dc.contributor.author	Bonjoch i Sesé, Josep
dc.date	2019-02-19T12:07:13Z
dc.date	2019-02-19T12:07:13Z
dc.date	2015-09-25
dc.date	2019-02-19T12:07:14Z
dc.identifier.citation	1523-7060
dc.identifier.citation	666641
dc.identifier.uri	http://hdl.handle.net/2445/128419
dc.format	4 p.
dc.format	application/pdf
dc.language.iso	eng
dc.publisher	American Chemical Society
dc.relation	Versió postprint del document publicat a: https://doi.org/10.1021/acs.orglett.5b02581
dc.relation	Organic Letters, 2015, vol. 17, num. 20, p. 5084-5087
dc.relation	https://doi.org/10.1021/acs.orglett.5b02581
dc.rights	(c) American Chemical Society , 2015
dc.rights	info:eu-repo/semantics/openAccess
dc.subject	Alcaloides
dc.subject	Compostos heterocíclics
dc.subject	Síntesi orgànica
dc.subject	Productes naturals
dc.subject	Alkaloids
dc.subject	Heterocyclic compounds
dc.subject	Organic synthesis
dc.subject	Natural products
dc.title	Approach to cis-Phlegmarine Alkaloids via Stereodivergent Reduction: Total Synthesis of (+)-Serratezomine E and Putative Structure of (−)-Huperzine N
dc.type	info:eu-repo/semantics/article
dc.type	info:eu-repo/semantics/acceptedVersion
dc.description.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.

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