Journal
CHEMICAL COMMUNICATIONS
Volume 52, Issue 99, Pages 14290-14293Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6cc08126f
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Funding
- DST-INDIA [EMR/2016/000041]
- CSIR, New Delhi, India
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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.
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