Selective 1,5-Alkylidenecarbene Insertion Reactions on [3.2.1] Oxabicyclic Ethers: a New Approach toward the AB Ring System of Ingenol

Research output: Contribution to journalArticle


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.


Original languageEnglish
Pages (from-to)2961-2964
Number of pages4
JournalOrganic Letters
Publication statusPublished - 1 Jan 2004