Attempted synthesis of central furopyran core of Diocollettines A via a Gold-Catalyzed cascade 1,6-Diyne cycloisomerization process

[Display omitted] •Diyne cycloisomerization.•Undesired regioselectivity.•Simple access to furopyran core. Herein, we describe an Au-catalyzed cascade diyne cycloisomerization process that was projected to construct the central furopyran bicyclic core of Diocollettines A. Our intended strategy for th...

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Bibliographic Details
Published in:Tetrahedron letters 2020-10, Vol.61 (40), p.152367, Article 152367
Main Authors: Mullapudi, Venkannababu, Ramana, Chepuri V.
Format: Article
Language:English
Subjects:
1,6-Hexadiyne
Alkynol cycloisomerization
Diocollettines A
Gold-catalysis
Total synthesis
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Summary:[Display omitted] •Diyne cycloisomerization.•Undesired regioselectivity.•Simple access to furopyran core. Herein, we describe an Au-catalyzed cascade diyne cycloisomerization process that was projected to construct the central furopyran bicyclic core of Diocollettines A. Our intended strategy for the annulation of the third thf ring is based on epoxidation and subsequent intramolecular acetalization. However, the initial alkynol cyclization occurred in an undesired 5-exo-dig mode, ultimately leading to an undesired furopyran.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.152367