Selectivity Control in Terpene Rearrangements: A Biomimetic Synthesis of the Halimanic Bicyclic Core
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SÎRBU, Tatiana; GÎRBU, Vladilena; HARGHEL, Petru; RUSU, Vasile; UNGUR, Nicon; KULCIŢKI, Veaceslav. Selectivity Control in Terpene Rearrangements: A Biomimetic Synthesis of the Halimanic Bicyclic Core. In: Synthesis (Germany). 2019, nr. 9(51), pp. 1995-2000. ISSN 0039-7881.
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Synthesis (Germany)
Numărul 9(51) / 2019 / ISSN 0039-7881

Selectivity Control in Terpene Rearrangements: A Biomimetic Synthesis of the Halimanic Bicyclic Core


DOI: 10.1055/s-0037-1610686
Pag. 1995-2000

Sîrbu Tatiana, Gîrbu Vladilena, Harghel Petru, Rusu Vasile, Ungur Nicon, Kulciţki Veaceslav
 
Institute of Chemistry
 
Disponibil în IBN: 2 mai 2019


Rezumat

The bicyclic core of the halimanic framework is synthesized in optically active form by an acid-induced rearrangement of a homo-drimanic epoxide. The substrate can follow two different pathways under acidic treatment. Using fluorosulfonic acid as a promoter at low temperature favors ring contraction to a perhydrindanic structure. In contrast, milder acids at higher temperatures bring about predominantly an angular methyl migration and formation of the halimanic bicyclic system. In particular, an acidic pillared clay selectively promoted this transformation.

Cuvinte-cheie
biomimetic synthesis, clays, heterogeneous catalysis, rearrangements, terpenoids