Selective 1,5-Alkylidenecarbene Insertion Reactions on [3.2.1] Oxabicyclic Ethers: a New Approach toward the AB Ring System of Ingenol
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Colleges, School and Institutes
Two methods to achieve the formal aldol reaction between acetone and two oxabicyclic [3.2.1] ketones are reported. The trimethylsilyl-protected beta-hydroxy ketones are converted by a Wittig reaction into vinyl chlorides as synthetic precursors to alkylidenecarbenes. Selective 1,5 C-H over 1,5 O-Si insertion has been applied to the synthesis of a model for the ABC ring system of ingenol.
|Number of pages||4|
|Publication status||Published - 1 Jan 2004|