2. Academic Validation
  3. Bioinspired Synthesis of Pygmaeocins and Related Rearranged Abietane Diterpenes: Synthesis of Viridoquinone

Bioinspired Synthesis of Pygmaeocins and Related Rearranged Abietane Diterpenes: Synthesis of Viridoquinone

  • Org Lett. 2018 Sep 21;20(18):5666-5670. doi: 10.1021/acs.orglett.8b02395.
Mustapha Ait El Had 1 2,  Juan J Guardia 2,  Jose M Ramos 2,  Moha Taourirte 1,  Rachid Chahboun 2,  Enrique Alvarez-Manzaneda 2
Affiliations

Affiliations

  • 1 Laboratoire de Chimie Biorganique et Macromoléculaire , Faculté des Sciences et Techniques de Marrakech (FSTGM), Université Cadi Ayyad Marrakech , 40000 Marrakech , Morocco.
  • 2 Departamento de Química Orgánica , Facultad de Ciencias, Universidad de Granada , 18071 Granada , Spain.
PMID: 30212217 DOI: 10.1021/acs.orglett.8b02395
Abstract

A bioinspired synthesis of rearranged abietane diterpenes, related to pygmaeocins, is described. In this process, the key step is the 1,2-migration of the C-20 angular methyl to the C-5 position of the abietane skeleton, which occurs when a C6-C7 unsaturated dehydroabietane derivative is treated with SeO2 in dioxane under reflux (19 examples for this rearrangement are described). Utilizing this reaction, an enantiospecific synthesis of pygmaeocin C and the first synthesis of viridoquinone, starting from the abietane phenol ferruginol, are reported. A tentative mechanism for this reaction and a possible biosynthetic pathway for this family of metabolites are postulated.

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