Mild Approach to 2‑Acylfurans via Intercepted Meyer–Schuster Rearrangement of 6‑Hydroxyhex-2-en-4-ynals

We
have developed a mild, intramolecular intercepted Meyer–Schuster
(M-S) rearrangement for the synthesis of 2-acylfurans from corresponding cis-6-hydroxyhex-2-en-4-ynals. This reaction was found to
be very general, and the starting materials are easily accessible.
By this methodology the first synthesis of deoxy-nor-abiesesquine B, a sesquiterpene, was also achieved in three steps.
The concept of adding two nucleophiles during the M-S rearrangement
was introduced.