An Enantioselective Synthesis of Cryptocarya Diacetate

The enantioselective synthesis of cryptocarya diacetate has been achieved in 10 steps from ethyl sorbate. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form a δ-hydroxy-1-enoate, which was subsequently converted into a benzylide...

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Bibliographic Details
Published inOrganic letters Vol. 3; no. 17; pp. 2777 - 2780
Main Authors Hunter, Thomas J, O'Doherty, George A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 23.08.2001
Amer Chemical Soc
Subjects
Acetates - chemical synthesis
Chemistry
Chemistry, Organic
Lauraceae - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
PALLADIUM
ASYMMETRIC-SYNTHESIS
5,6-DIHYDRO-ALPHA-PYRONES
ALPHA-PYRONES
CONFIGURATION
ESTERS
FRAGMENT
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Summary:The enantioselective synthesis of cryptocarya diacetate has been achieved in 10 steps from ethyl sorbate. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form a δ-hydroxy-1-enoate, which was subsequently converted into a benzylidene-protected 3,5-dihydroxy carboxylic ester. This ester was converted into cryptocarya diacetate in 14% overall yield via an allylation and methathesis ring closure reaction sequence.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol016399t