Highly stereloselective and stereodivergent synthesis of four types of THF cores in acetogenins using a C-4-chiral building block

Four stereoisomers of the THF cores, synthetic intermediates of acetogenins, have been synthesized with high diastereoselectivity by asymmetric alkynylation and subsequent stereodivergent THF ring formation. The asymmetric alkynylation of alpha-oxyaldehyde with (S)-3-butyne-1,2-diol derivatives (C-4...

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Bibliographic Details
Published inOrganic letters Vol. 4; no. 17; pp. 2977 - 2980
Main Authors Maezaki, N, Kojima, N, Asai, M, Tominaga, H, Tanaka, T
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 22.08.2002
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
HYDROGENOLYSIS
INHIBITION
SATURATED OXYGEN HETEROCYCLES
ALDEHYDES
ENANTIOSELECTIVE ADDITION
ANNONACEOUS ACETOGENINS
ACETATE
IN-SITU GENERATION
STEREOSELECTIVE SYNTHESIS
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Summary:Four stereoisomers of the THF cores, synthetic intermediates of acetogenins, have been synthesized with high diastereoselectivity by asymmetric alkynylation and subsequent stereodivergent THF ring formation. The asymmetric alkynylation of alpha-oxyaldehyde with (S)-3-butyne-1,2-diol derivatives (C-4-unit) gave good yields of syn and anti adducts with >97:3 dr and 94:6 dr, respectively. These adducts were converted into the four types of THF compounds via one-pot THF formation or via intramolecular Williamson synthesis.
ISSN:1523-7060
DOI:10.1021/ol026393j