Abstract
A convergent synthesis of the title compounds is reported, which relies on a successive 2-fold SN'-type substitution reaction at methoxy-substituted propargylic acetates. The furan C3-C4 bond is presumably established by silyl enol ether attack at a propargylic cation intermediate. The resulting α-methoxyallene is intramolecularly substituted, leading to cyclization by displacement of the methoxy group (O-C2 bond formation) and to simultaneous formation of the exocyclic alkene double bond. Despite the relatively mild conditions, the reactions were complete within 5 min.
Original language | English |
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Pages (from-to) | 6372-6379 |
Number of pages | 8 |
Journal | Journal of Organic Chemistry |
Volume | 79 |
Issue number | 13 |
DOIs | |
State | Published - 3 Jul 2014 |