A synthetic approach to the furanocembrane carbon skeleton by a regio-selective bromine-magnesium exchange reaction

Christoph Stock; Frank Höfer; Thorsten Bach

doi:10.1055/s-2004-837229

A synthetic approach to the furanocembrane carbon skeleton by a regio-selective bromine-magnesium exchange reaction

Christoph Stock
, Frank Höfer
, Thorsten Bach

Chair of Organic Chemistry

Technical University of Munich

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

25 Scopus citations

Abstract

The dibromofuran 6 was prepared in four steps from dibromofurfural 3 in 73% yield. It was regioselectively metalated by a bromine-magnesium exchange reaction and was added to aldehyde 7. Alcohol 8 was obtained by this key step in 75% yield. Further functionalization reactions led to the precursors 17-19 for an intramolecular Nozaki-Hiyama coupling. The ring-closing Nozaki-Hiyama protocol was successfully implemented in the synthesis of the macrocyclic propargylic alcohol 20.

Original language	English
Pages (from-to)	511-513
Number of pages	3
Journal	Synlett
Issue number	3
DOIs	https://doi.org/10.1055/s-2004-837229
State	Published - 16 Feb 2005

Keywords

Cross-coupling
Furans
Metalations
Natural products
Terpenoids

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10.1055/s-2004-837229

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abstract = "The dibromofuran 6 was prepared in four steps from dibromofurfural 3 in 73\% yield. It was regioselectively metalated by a bromine-magnesium exchange reaction and was added to aldehyde 7. Alcohol 8 was obtained by this key step in 75\% yield. Further functionalization reactions led to the precursors 17-19 for an intramolecular Nozaki-Hiyama coupling. The ring-closing Nozaki-Hiyama protocol was successfully implemented in the synthesis of the macrocyclic propargylic alcohol 20.",

keywords = "Cross-coupling, Furans, Metalations, Natural products, Terpenoids",

author = "Christoph Stock and Frank H{\"o}fer and Thorsten Bach",

year = "2005",

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doi = "10.1055/s-2004-837229",

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T1 - A synthetic approach to the furanocembrane carbon skeleton by a regio-selective bromine-magnesium exchange reaction

AU - Stock, Christoph

AU - Höfer, Frank

AU - Bach, Thorsten

PY - 2005/2/16

Y1 - 2005/2/16

N2 - The dibromofuran 6 was prepared in four steps from dibromofurfural 3 in 73% yield. It was regioselectively metalated by a bromine-magnesium exchange reaction and was added to aldehyde 7. Alcohol 8 was obtained by this key step in 75% yield. Further functionalization reactions led to the precursors 17-19 for an intramolecular Nozaki-Hiyama coupling. The ring-closing Nozaki-Hiyama protocol was successfully implemented in the synthesis of the macrocyclic propargylic alcohol 20.

AB - The dibromofuran 6 was prepared in four steps from dibromofurfural 3 in 73% yield. It was regioselectively metalated by a bromine-magnesium exchange reaction and was added to aldehyde 7. Alcohol 8 was obtained by this key step in 75% yield. Further functionalization reactions led to the precursors 17-19 for an intramolecular Nozaki-Hiyama coupling. The ring-closing Nozaki-Hiyama protocol was successfully implemented in the synthesis of the macrocyclic propargylic alcohol 20.

KW - Cross-coupling

KW - Furans

KW - Metalations

KW - Natural products

KW - Terpenoids

UR - https://www.scopus.com/pages/publications/14644416508

U2 - 10.1055/s-2004-837229

DO - 10.1055/s-2004-837229

M3 - Article

AN - SCOPUS:14644416508

SN - 0936-5214

SP - 511

EP - 513

JO - Synlett

JF - Synlett

IS - 3

ER -

A synthetic approach to the furanocembrane carbon skeleton by a regio-selective bromine-magnesium exchange reaction

Abstract

Keywords

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