Bicyclic oxygen heterocycles from γ,δ-unsaturated alcohols: Synthetic targets inspired by blepharocalyxin D

Adam J. Bunt; Christopher D. Bailey; Benjamin D. Cons; Sophie J. Edwards; Jon D. Elsworth; Tshepo Pheko; Christine L. Willis

doi:10.1002/anie.201108315

Bicyclic oxygen heterocycles from γ,δ-unsaturated alcohols: Synthetic targets inspired by blepharocalyxin D

Adam J. Bunt
, Christopher D. Bailey
, Benjamin D. Cons
, Sophie J. Edwards
, Jon D. Elsworth
, Tshepo Pheko
, Christine L. Willis

Chemical & Forensic Sciences

Research output: Contribution to journal › Article › peer-review

48 Citations (Scopus)

Abstract

trans-2,8-Dioxabicyclodecanes were prepared in high yield with the creation of up to three stereocenters in a single pot by the acid-mediated reaction of γ,δ-unsaturated alcohols with aldehydes (see scheme, Bn=benzyl). This versatile reaction enables the stereoselective introduction of substituents at the C3, C4, C7, and C9 positions of the bicyclic framework.

Original language	English
Pages (from-to)	3901-3904
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	16
DOIs	https://doi.org/10.1002/anie.201108315
Publication status	Published - Apr 16 2012

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry

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abstract = "trans-2,8-Dioxabicyclodecanes were prepared in high yield with the creation of up to three stereocenters in a single pot by the acid-mediated reaction of γ,δ-unsaturated alcohols with aldehydes (see scheme, Bn=benzyl). This versatile reaction enables the stereoselective introduction of substituents at the C3, C4, C7, and C9 positions of the bicyclic framework.",

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AU - Bunt, Adam J.

AU - Bailey, Christopher D.

AU - Cons, Benjamin D.

AU - Edwards, Sophie J.

AU - Elsworth, Jon D.

AU - Pheko, Tshepo

AU - Willis, Christine L.

PY - 2012/4/16

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AB - trans-2,8-Dioxabicyclodecanes were prepared in high yield with the creation of up to three stereocenters in a single pot by the acid-mediated reaction of γ,δ-unsaturated alcohols with aldehydes (see scheme, Bn=benzyl). This versatile reaction enables the stereoselective introduction of substituents at the C3, C4, C7, and C9 positions of the bicyclic framework.

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Bicyclic oxygen heterocycles from γ,δ-unsaturated alcohols: Synthetic targets inspired by blepharocalyxin D

Abstract

All Science Journal Classification (ASJC) codes

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