Total synthesis of (-)-dysiherbaine

The enantioselective synthesis of (-)-dysiherbaine (1) has been established with efficiency via a unique synthetic strategy involving the desymmetrization of 2-substituted glycerol to install a quaternary chiral carbon, which induces further stereochemistry in the bicyclic perhydrofuropyran through...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2012-06, Vol.48 (50), p.6295-6297
Main Authors: Celindro, Nelma Carurucan, Kim, Tae Woo, Kang, Sung Ho
Format: Article
Language:English
Subjects:
Alanine - analogs & derivatives
Alanine - chemical synthesis
Alanine - chemistry
Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Carbon
Carbon-epoxy composites
Epoxidation
Glycerols
Molecular Conformation
Stereochemistry
Stereoisomerism
Strategy
Synthesis
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Summary:The enantioselective synthesis of (-)-dysiherbaine (1) has been established with efficiency via a unique synthetic strategy involving the desymmetrization of 2-substituted glycerol to install a quaternary chiral carbon, which induces further stereochemistry in the bicyclic perhydrofuropyran through mercuriocyclization and epoxidation.
ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc32736h