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El Had MA, Guardia JJ, Ramos JM, et al. Bioinspired Synthesis of Pygmaeocins and Related Rearranged Abietane Diterpenes: Synthesis of Viridoquinone. Org Lett. 2018;20(18):5666-5670doi: 10.1021/acs.orglett.8b02395.
El Had, M. A., Guardia, J. J., Ramos, J. M., Taourirte, M., Chahboun, R., & Alvarez-Manzaneda, E. (2018). Bioinspired Synthesis of Pygmaeocins and Related Rearranged Abietane Diterpenes: Synthesis of Viridoquinone. Organic letters, 20(18), 5666-5670. https://doi.org/10.1021/acs.orglett.8b02395
El Had, Mustapha Ait, et al. "Bioinspired Synthesis of Pygmaeocins and Related Rearranged Abietane Diterpenes: Synthesis of Viridoquinone." Organic letters vol. 20,18 (2018): 5666-5670. doi: https://doi.org/10.1021/acs.orglett.8b02395
El Had MA, Guardia JJ, Ramos JM, Taourirte M, Chahboun R, Alvarez-Manzaneda E. 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. Epub 2018 Sep 13. PMID: 30212217.
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Org Lett. 2018 Sep 21;20(18):5666-5670. doi: 10.1021/acs.orglett.8b02395. Epub 2018 Sep 13.

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

Organic letters

Mustapha Ait El Had, Juan J Guardia, Jose M Ramos, Moha Taourirte, Rachid Chahboun, Enrique Alvarez-Manzaneda

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 SeO

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