A convergent synthesis of the tricyclic core of the dictyosphaeric acids

Christopher W. Barfoot; Alan R. Burns; Michael G. Edwards; Martin N. Kenworthy; Mahmood Ahmed; Stephen E. Shanahan; Richard J. K. Taylor

doi:10.1021/ol702887e

A convergent synthesis of the tricyclic core of the dictyosphaeric acids

Christopher W. Barfoot, Alan R. Burns, Michael G. Edwards, Martin N. Kenworthy, Mahmood Ahmed, Stephen E. Shanahan, Richard J. K. Taylor

Chemistry

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

Abstract

The first synthetic route to the tricyclic core of the dictyosphaeric acids has been established starting from readily available (S)-(-)-4-(tert-butyldimethylsilyloxy)cyclohexenone and involving 9 steps, including a ring-closing metathesis to produce a 13-membered macrolactone, and a doubly tethered intramolecular Michael addition.

Original language	English
Pages (from-to)	353-356
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	2
DOIs	https://doi.org/10.1021/ol702887e
Publication status	Published - 17 Jan 2008

Keywords

MICHAEL REACTION
4-HYDROXYCYCLOHEX-2-ENONE

Access to Document

10.1021/ol702887e

Cite this

@article{ae9e9a6de462405ab403810728756106,

title = "A convergent synthesis of the tricyclic core of the dictyosphaeric acids",

abstract = "The first synthetic route to the tricyclic core of the dictyosphaeric acids has been established starting from readily available (S)-(-)-4-(tert-butyldimethylsilyloxy)cyclohexenone and involving 9 steps, including a ring-closing metathesis to produce a 13-membered macrolactone, and a doubly tethered intramolecular Michael addition.",

keywords = "MICHAEL REACTION, 4-HYDROXYCYCLOHEX-2-ENONE",

author = "Barfoot, {Christopher W.} and Burns, {Alan R.} and Edwards, {Michael G.} and Kenworthy, {Martin N.} and Mahmood Ahmed and Shanahan, {Stephen E.} and Taylor, {Richard J. K.}",

year = "2008",

month = jan,

day = "17",

doi = "10.1021/ol702887e",

language = "English",

volume = "10",

pages = "353--356",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "2",

}

TY - JOUR

T1 - A convergent synthesis of the tricyclic core of the dictyosphaeric acids

AU - Barfoot, Christopher W.

AU - Burns, Alan R.

AU - Edwards, Michael G.

AU - Kenworthy, Martin N.

AU - Ahmed, Mahmood

AU - Shanahan, Stephen E.

AU - Taylor, Richard J. K.

PY - 2008/1/17

Y1 - 2008/1/17

N2 - The first synthetic route to the tricyclic core of the dictyosphaeric acids has been established starting from readily available (S)-(-)-4-(tert-butyldimethylsilyloxy)cyclohexenone and involving 9 steps, including a ring-closing metathesis to produce a 13-membered macrolactone, and a doubly tethered intramolecular Michael addition.

AB - The first synthetic route to the tricyclic core of the dictyosphaeric acids has been established starting from readily available (S)-(-)-4-(tert-butyldimethylsilyloxy)cyclohexenone and involving 9 steps, including a ring-closing metathesis to produce a 13-membered macrolactone, and a doubly tethered intramolecular Michael addition.

KW - MICHAEL REACTION

KW - 4-HYDROXYCYCLOHEX-2-ENONE

UR - http://www.scopus.com/inward/record.url?scp=38749122493&partnerID=8YFLogxK

U2 - 10.1021/ol702887e

DO - 10.1021/ol702887e

M3 - Article

SN - 1523-7060

VL - 10

SP - 353

EP - 356

JO - Organic Letters

JF - Organic Letters

IS - 2

ER -

A convergent synthesis of the tricyclic core of the dictyosphaeric acids

Abstract

Keywords

Access to Document

Other files and links

Cite this