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Literature DB >> 20722386

Highly α-selective hydrolysis of α,β-epoxyalcohols using tetrabutylammonium fluoride.

Purba Mukerjee¹, Mohammed Abid, Frank C Schroeder.

Abstract

We report a simple method for the highly regio- and stereoselective hydrolysis of α,β-epoxyalcohols. Treatment of enantiopure epoxyalcohols derived from Sharpless epoxidation with TBAF/H(2)O resulted in exclusive ring opening at the normally disfavored α-position, providing access to arabino- or lyxo-configured triols with full preservation of stereochemical purity. The method was applied in syntheses of 5-deoxy-l-arabinose (26) and a family of bicyclic acetals based on the insect pheromone hydroxybrevicomin (4).

Entities: Chemical Disease Gene

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Year: 2010 PMID： 20722386 PMCID： PMC2937070 DOI： 10.1021/ol1015306

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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References

9 in total

9. Identification and synthesis of new bicyclic acetals from the mountain pine beetle, Dendroctonus ponderosae Hopkins (Col.: Scol.).

Authors: W Francke; F Schröder; P Philipp; H Meyer; V Sinnwell; G Gries
Journal: Bioorg Med Chem Date: 1996-03 Impact factor: 3.641

9 in total

Highly α-selective hydrolysis of α,β-epoxyalcohols using tetrabutylammonium fluoride.

1. Chemoenzymatic synthesis of (+)-aspicilin from chlorobenzene.

2. A Total Synthesis of FK-506(1).

3. A short and efficient stereoselective synthesis of the polyhydroxylated macrolactone (+)-aspicillin

4. Total Synthesis of (+)-Aspicilin. The Naked Carbon Skeleton Strategy vs the Bioorganic Approach.

5. Epoxide-opening cascades promoted by water.

6. Brevicomin: principal sex attractant in the frass of the female western pine beetle.

7. New building block for polyhydroxylated piperidine: total synthesis of 1,6-dideoxynojirimycin.

8. Frontalin: a chemical message of musth in Asian elephants (Elephas maximus).

9. Identification and synthesis of new bicyclic acetals from the mountain pine beetle, Dendroctonus ponderosae Hopkins (Col.: Scol.).