Synthesis of ent‐Kaurane and Beyerane Diterpenoids by Controlled Fragmentations of Overbred Intermediates

2013/07/16 by Emily C. Cherney, Jason C. Green, Phil S. Baran · 1 citation
Biochemistry, Genetics and Molecular Biology · Medicine · #Bioactive Natural Diterpenoids Research #Biological and pharmacological studies of plants #Biological Activity of Diterpenoids and Biflavonoids

paper · doi:10.1002/anie.201304609

openalex publication_date 2013/07/16 · openalex created_date 2016/06/24 · openalex updated_date 2026/07/27

Abstract

Efficient access to minimally oxidized members of the ent-kaurane and beyerane class of terpenes has been achieved by using a polyene cyclization precursor designed to directly yield oxidation at the axial C19-methyl group. Construction of the [3.2.1]bicyclic system found in the ent-kaurane skeleton was realized with two overbred intermediates. Wagner–Meerwein rearrangement of the [3.2.1]bicyclic system yields the beyerane skeleton of isosteviol.

Citations

• Zur Kenntnis der Triterpene. 190. Mitteilung. Eine stereochemische Interpretation der biogenetischen Isoprenregel bei den Triterpenen
• Diterpenoids from Isodon species and their biological activities
• On the stereochemistry of photoaddition between α,β-unsaturated ketones and olefins

Cited by

• Allene [wikipedia]

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