The first biomimetic synthesis of a diterpenoid with the ent-verrucosin A/B skeleton

Grinco Marina; Gîrbu Vladilena; Gorincioi Elena; Barba Alic; Kulciţki Veaceslav; Ungur Nikon

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GRINCO, Marina, GÎRBU, Vladilena, GORINCIOI, Elena, BARBA, Alic, KULCIŢKI, Veaceslav, UNGUR, Nikon. The first biomimetic synthesis of a diterpenoid with the ent-verrucosin A/B skeleton. In: Tetrahedron Letters, 2016, nr. 19(57), pp. 2084-2096. ISSN 0040-4039. DOI: https://doi.org/10.1016/j.tetlet.2016.03.106

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Tetrahedron Letters

Numărul 19(57) / 2016 / ISSN 0040-4039

The first biomimetic synthesis of a diterpenoid with the ent-verrucosin A/B skeleton

DOI:https://doi.org/10.1016/j.tetlet.2016.03.106

Pag. 2084-2096

Grinco Marina, Gîrbu Vladilena, Gorincioi Elena, Barba Alic, Kulciţki Veaceslav, Ungur Nikon

Institute of Chemistry of the Academy of Sciences of Moldova

Disponibil în IBN: 12 septembrie 2022

Rezumat

The first biomimetic synthesis of methyl (8S,9R,13R,14R)-4,4,8,9,13-pentamethyl-20(10 → 9)-abeo-ent-isocopal-5(10),11(12)-dien-15-oate - a diterpenoid with the ent-verrucosin A/B skeleton has been performed by electrophilic isomerization of methyl 12α-hydroxy-ent-isocopal-13(16)-en-15-oate. The structure and stereochemistry of the synthesized compound have been established on the basis of spectroscopic data.

Cuvinte-cheie
biomimetic synthesis, diterpenoids, Isomerization, Verrucosin A

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