Syntheses and structural confirmations of members of a heterocycle- containing family of labdane diterpenoids

Daniel J. MacK; Jon T. Njardarson

doi:10.1002/anie.201208412

Syntheses and structural confirmations of members of a heterocycle- containing family of labdane diterpenoids

Daniel J. MacK, Jon T. Njardarson

Research output: Contribution to journal › Article › peer-review

22 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	1543-1547
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	5
DOIs	https://doi.org/10.1002/anie.201208412
State	Published - Jan 28 2013

Keywords

labdanes
olefin isomerization
ring expansion
total synthesis
vinyl oxiranes

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201208412

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abstract = "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.",

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KW - total synthesis

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Syntheses and structural confirmations of members of a heterocycle- containing family of labdane diterpenoids

Abstract

Keywords

ASJC Scopus subject areas

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