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

Richard Grainger; RB Owoare

doi:10.1021/ol048911r

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

Richard Grainger, RB Owoare

Chemistry

Research output: Contribution to journal › Article

23 Citations (Scopus)

Abstract

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 language	English
Pages (from-to)	2961-2964
Number of pages	4
Journal	Organic Letters
Volume	6
DOIs	https://doi.org/10.1021/ol048911r
Publication status	Published - 1 Jan 2004

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abstract = "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.",

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AB - 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.

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

Abstract

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