Enantio- and Diastereoselective Synthesis of (E)-1,5-syn-Diols: Application to the Synthesis of the C(23)−C(40) Fragment of Tetrafibricin

A highly stereoselective synthesis of (E)-1,5-syn-diols 6 is described. The kinetically controlled hydroboration of allenyltrifluoroborate 8 with Soderquist borane 2 provides the (Z)-allylic trifluoroborate 9, which undergoes sequential allylboration with two different aldehydes to provide (E)-1,5-s...

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Bibliographic Details
Published inOrganic letters Vol. 13; no. 7; pp. 1868 - 1871
Main Authors Kister, Jeremy, Nuhant, Philippe, Lira, Ricardo, Sorg, Achim, Roush, William R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.04.2011
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Kinetics
Macrolides - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
ASYMMETRIC ALLYLBORATION
AMPHIDINOL 3
ENANTIOSELECTIVE SYNTHESIS
MARINE ACTINOMYCETE
CONFIGURATION
DOUBLE-ALLYLBORATION REACTION
GPIIB/IIIA
STEREOSELECTIVE-SYNTHESIS
STREPTOMYCES-NEYAGAWAENSIS
FIBRINOGEN RECEPTOR ANTAGONIST
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Summary:A highly stereoselective synthesis of (E)-1,5-syn-diols 6 is described. The kinetically controlled hydroboration of allenyltrifluoroborate 8 with Soderquist borane 2 provides the (Z)-allylic trifluoroborate 9, which undergoes sequential allylboration with two different aldehydes to provide (E)-1,5-syn-diols 6 in 72−98% yields with >95% ee and >20:1 dr. Application of this method to the synthesis of the tetrafibricin C(23)−C(40) fragment 19 is described.
Bibliography:NIH RePORTER
ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol2003836