Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 68, Issue 20, Pages 7841-7844Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo034738l
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Funding
- NIAID NIH HHS [AI-50888, R01 AI050888-02, R01 AI050888] Funding Source: Medline
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Four unique diastereomers of 3-hydroxy-2,4,6-trimethylheptanoic acid-(2R,3R,4R), (2S,3R,4R), (2S,3R,4S), and (2R,3R,4S)-the fatty acid component of callipeltin A and D, have been synthesized from commercially available (+)- and (-)-pseudoephedrine propionamide in 6 steps and 59% average overall yield. Comparison of the H-1 and C-13 NMR and optical rotation data of the resulting isomers with the natural fragment unambiguously verifies the configurational assignment of the natural isomer as (2R,3R,4R).
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