Literature DB >> 25648434

Synthesis of mulinane diterpenoids.

Keith P Reber1, Jing Xu, Carlos A Guerrero.   

Abstract

The mulinane class of diterpenoids is a set of tricyclic (5-6-7), biologically active natural products whose members exhibit a variety of oxidation states. Herein, we report the inaugural synthesis of four mulinanes employing a divergent approach that relies on a diastereoselective anionic oxy-Cope rearrangement to set the relative configuration of the C8 stereocenter and an unprecedented vinylogous Saegusa dehydrogenation reaction to address C-ring functionality.

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Year:  2015        PMID: 25648434     DOI: 10.1021/jo502602u

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  4 in total

Review 1.  Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.

Authors:  Nicole D Bartolo; Jacquelyne A Read; Elizabeth M Valentín; K A Woerpel
Journal:  Chem Rev       Date:  2020-01-06       Impact factor: 60.622

2.  Formation of trisubstituted buta-1,3-dienes and α,β-unsaturated ketones via the reaction of functionalized vinyl phosphates and vinyl phosphordiamidates with organometallic reagents.

Authors:  Petr Oeser; Jakub Koudelka; Hana Dvořáková; Tomáš Tobrman
Journal:  RSC Adv       Date:  2020-09-22       Impact factor: 4.036

Review 3.  Mulinane- and Azorellane-Type Diterpenoids: A Systematic Review of Their Biosynthesis, Chemistry, and Pharmacology.

Authors:  Angel de Jesús Dzul-Beh; Andrés Humberto Uc-Cachón; Jorge Bórquez; Luis A Loyola; Luis Manuel Peña-Rodríguez; Gloria María Molina-Salinas
Journal:  Biomolecules       Date:  2020-09-17

4.  Activity of Semi-Synthetic Mulinanes against MDR, Pre-XDR, and XDR Strains of Mycobacterium tuberculosis.

Authors:  María Alejandrina Martínez-González; Luis Manuel Peña-Rodríguez; Andrés Humberto Uc-Cachón; Jorge Bórquez; Mario J Simirgiotis; Hugo Brígido Barrios-García; Rogelio Hernández-Pando; Luis Alberto Loyola; Carlos Areche; Angel de Jesús Dzul-Beh; Jorge Alberto Barrios-Payán; Dulce Mata-Espinosa; Fabiola Escalante-Erosa; Karlina García-Sosa; Gloria María Molina-Salinas
Journal:  Metabolites       Date:  2021-12-16
  4 in total

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