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2015-09-25

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/128419

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

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https://doi.org/10.1021/acs.orglett.5b02581

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

Alcaloides, Compostos heterocíclics, Síntesi orgànica, Productes naturals

Subject (English)

Alkaloids, Heterocyclic compounds, Organic synthesis, Natural products

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Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
Articles publicats en revistes (Institut de Biomedicina (IBUB))

Citation

BOSCH, Caroline, et al. Approach to cis-Phlegmarine Alkaloids via Stereodivergent Reduction: Total Synthesis of (+)-Serratezomine E and Putative Structure of (−)-Huperzine N. Organic Letters. 2015. Vol. 17, num. 20, pags. 5084-5087. ISSN 1523-7060. [consulted: 15 of August of 2026]. Available at: https://hdl.handle.net/2445/128419

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