Regioselective, cascade [3+2] annulation of beta-naphthols (resorcinols) with Z-enoate propargylic alcohols: a novel entry for the synthesis of complex naphtho(benzo)furans

An acid promoted, unprecedented cascade [3+2] annulation strategy for the synthesis of complex naphtho-and benzofurans is reported. An alkoxyfuranylallene intermediate (generated from Z-enoate propargylic alcohols via a Meyer-Schuster rearrangement) was employed as the 1,2-bis-electrophile and b-nap...

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Published inChemical communications (Cambridge, England) Vol. 52; no. 99; pp. 14290 - 14293
Main Authors Tharra, Prabhakararao, Baire, Beeraiah
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2016
Subjects
Alcohols
Biocompatibility
Cascades
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Organic chemistry
Phenols
Physical Sciences
Science & Technology
Strategy
Synthesis
ORGANIC-SYNTHESIS
CYCLOADDITION
ANTIBIOTICS
ACID
HETEROCYCLES
CONSTRUCTION
SESQUITERPENE HYDROQUINONE DERIVATIVES
INHIBITOR
2,3-DISUBSTITUTED BENZOFURANS
PHENOL DERIVATIVES
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Summary:An acid promoted, unprecedented cascade [3+2] annulation strategy for the synthesis of complex naphtho-and benzofurans is reported. An alkoxyfuranylallene intermediate (generated from Z-enoate propargylic alcohols via a Meyer-Schuster rearrangement) was employed as the 1,2-bis-electrophile and b-naphthols ( phenols) as 1,3-bisnucleophiles. This strategy represents the first cascade and metal free process for the synthesis of naphthofurans and benzofurans from propargylic alcohols. A very broad substrate scope was observed. The synthesized naphtho-and benzofuranswere efficiently transformed into the frameworks of the bioactive natural products amycofuran and frondosin B.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc08126f