Tetrahedron p. 7171 - 7178 (1991)
Update date:2022-07-30
Topics:
Curtis, Neil R.
Holmes, Andrew B.
Looney, Mark G.
An advanced intermediate for the synthesis of the Laurencia oxonane natural product obtusenyne 1, namely the unsaturated nine-membered lactone 3, was efficiently prepared in seven steps from (E)-3-hexenoic acid 7.The key transformation was the Claisen rearrangement of the vinyl ketene acetal 4, which represents novel methodology for the preparation of such unsaturated nine-membered lactones. Key words: medium ring; unsaturated lactone; Claisen rearrangement; vinyl ketene acetal; selenoxide elimination.
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