Novel protection of 1,2-diol for trans-dihydroxycyclopentene ring construction by the C-H insertion of alkylidene carbene: Formal total synthesis of (+)-trehazolin

The chiral vicinal diol was protected as 6-methylene-1,4-dioxepane to construct a cyclopentene ring by the C-H insertion of alkylidene carbene. The removal of the protecting group was achieved in a few steps, affording the corresponding diol in a reasonable yield. Using these reactions, the known sy...

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Bibliographic Details
Published inTetrahedron letters Vol. 60; no. 39; pp. 151085 - 151088
Main Authors Ohira, Susumu, Kuboki, Atsuhito, Takimoto, Yoshimi, Matsuda, Kyosuke, Itasaki, Saori, Urushibata, Yuki, Takano, Yoshiyuki, Nakamura, Yuuki
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.09.2019
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Glycosidase inhibitor
Protecting group
TREHAZOLIN
C-H insertion
Alkylidene carbene
AMINOCYCLITOL MOIETY
TRIMETHYLSILYLDIAZOMETHANE
STEREOCONTROLLED SYNTHESIS
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Summary:The chiral vicinal diol was protected as 6-methylene-1,4-dioxepane to construct a cyclopentene ring by the C-H insertion of alkylidene carbene. The removal of the protecting group was achieved in a few steps, affording the corresponding diol in a reasonable yield. Using these reactions, the known synthetic intermediate for (+)-trehazolin was synthesized from D-diethyl tartrate. In addition, a short route to the intermediate from a D-mannitol derivative was described. (C) 2019 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2019.151085