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Syntheses and Structural Confirmations of Members of a Heterocycle‐Containing Family of Labdane Diterpenoids
Author(s) -
Mack Daniel J.,
Njardarson Jon T.
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201208412
Subject(s) - labdane , isomerization , reagent , chemistry , ring (chemistry) , diene , organic chemistry , combinatorial chemistry , catalysis , diterpene , natural rubber
Building with berries! Several labdane natural products have been synthesized for the first time by the combination of a copper‐catalyzed vinyl oxirane ring expansion reaction with an abundant, inexpensive, chiral natural source (juniper berries; see scheme). These expedient (1–5 step) syntheses have resulted in the structural confirmations of five natural products and one reassignment. Reagent‐controlled oxidation and 1,3‐diene isomerization results are also presented.