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

Research output: Contribution to journalArticle

45 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 languageEnglish
Pages (from-to)3901-3904
Number of pages4
JournalAngewandte Chemie - International Edition
Volume51
Issue number16
DOIs
Publication statusPublished - Apr 16 2012

Fingerprint

Aldehydes
Alcohols
Oxygen
Acids
blepharocalyxin D

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Bunt, Adam J. ; Bailey, Christopher D. ; Cons, Benjamin D. ; Edwards, Sophie J. ; Elsworth, Jon D. ; Pheko, Tshepo ; Willis, Christine L. / Bicyclic oxygen heterocycles from γ,δ-unsaturated alcohols : Synthetic targets inspired by blepharocalyxin D. In: Angewandte Chemie - International Edition. 2012 ; Vol. 51, No. 16. pp. 3901-3904.
@article{54657b15e9bb46cdbebfba4bf1424ee6,
title = "Bicyclic oxygen heterocycles from γ,δ-unsaturated alcohols: Synthetic targets inspired by blepharocalyxin D",
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.",
author = "Bunt, {Adam J.} and Bailey, {Christopher D.} and Cons, {Benjamin D.} and Edwards, {Sophie J.} and Elsworth, {Jon D.} and Tshepo Pheko and Willis, {Christine L.}",
year = "2012",
month = "4",
day = "16",
doi = "10.1002/anie.201108315",
language = "English",
volume = "51",
pages = "3901--3904",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "16",

}

Bicyclic oxygen heterocycles from γ,δ-unsaturated alcohols : Synthetic targets inspired by blepharocalyxin D. / Bunt, Adam J.; Bailey, Christopher D.; Cons, Benjamin D.; Edwards, Sophie J.; Elsworth, Jon D.; Pheko, Tshepo; Willis, Christine L.

In: Angewandte Chemie - International Edition, Vol. 51, No. 16, 16.04.2012, p. 3901-3904.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Bicyclic oxygen heterocycles from γ,δ-unsaturated alcohols

T2 - Synthetic targets inspired by blepharocalyxin D

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

Y1 - 2012/4/16

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=84859743149&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84859743149&partnerID=8YFLogxK

U2 - 10.1002/anie.201108315

DO - 10.1002/anie.201108315

M3 - Article

C2 - 22392806

AN - SCOPUS:84859743149

VL - 51

SP - 3901

EP - 3904

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 16

ER -