Attempted synthesis of central furopyran core of diocollettines A via a gold-catalyzed cascade 1,6-diyne cycloisomerization process

TitleAttempted synthesis of central furopyran core of diocollettines A via a gold-catalyzed cascade 1,6-diyne cycloisomerization process
Publication TypeJournal Article
Year of Publication2020
AuthorsMullapudi, V, ,
JournalTetrahedron Letters
Volume61
Issue40
Pagination152367
Date PublishedOCT
Type of ArticleArticle
ISSN0040-4039
Keywords1, 6-Hexadiyne, Alkynol cycloisomerization, Diocollettines A, Gold-catalysis, Total synthesis
Abstract

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. (C) 2020 Elsevier Ltd. All rights reserved.
DOI10.1016/j.tetlet.2020.152367
Type of Journal (Indian or Foreign)

Foreign
Impact Factor (IF)

2.275
Divison category: 
Organic Chemistry

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