Publications by Maris Turks | EPFL Graph Search

Related publications (12)

Umpolung with Sulfur Dioxide: Carbon-Carbon Cross-Coupling of Electron-Rich 1,3-Dienes and Alkenes; Application to the Enantioselective Synthesis of Long-Chain Polyketide Fragments

Pierre Vogel, Maris Turks, Claudia Jana Exner

At low temperature and in the presence of an acid catalyst, sulfur dioxide undergoes hetero-Diels-Alder additions with 1-oxy-1,3-dienes, giving unstable sultines, which are ionized into zwitterionic species and react as 1-oxyallylic cation intermediates (U ...

2009

Synthesis of (E,Z)-1-Alkoxy-3-acyloxy-2-methylpenta-1,3-dienes via Danishefsky-Type Dienes or O-Acylation of Enones

Pierre Vogel, Maris Turks, Claudia Jana Exner

1-Alkoxy-2-methyl-3-acyloxy-(E,E)-penta-1,3-dienes have been prepared applying among others a modified Danishefsky's general method, including chiral, racemic, and achiral derivatives. ...

2009

Use of sultines in the asymmetric synthesis of polypropionate antibiotics

Pierre Vogel, Maris Turks, Laure Bouchez, Cotinica Craita, Xiaogen Huang, Freddy Fonquerne

At low temperature and in the presence of an acid catalyst, SO2 adds to 1,3-dienes equilibrating with the corresponding 3,6-dihydro-1,2-oxathiin-2-oxides (sultines). These compounds are unstable above -60 degrees C and equilibrate with the more stable 2,5- ...

De Gruyter2008

Expeditious asymmetric synthesis of a stereoheptad corresponding to the C(19)-C(27)-ansa chain of rifamycins: Formal total synthesis of Rifamycin S

Pierre Vogel, Maris Turks, Xiaogen Huang

In the presence of sulfur dioxide and an acid promoter, (-)-(1E,3Z)-2-methyl-1-((1S)-1-phenyleth- oxy)penta-1,3-dien-3-yl isobutyrate reacts with (Z)-3-(trimethylsilyloxy)-pent-2-ene giving a silyl sulfinate intermediate that undergoes, in the presence of ...

2005

Total Asymmetric Syntheses of beta-Hydroxy-delta-lactones via Umpolung with Sulfur Dioxide

Pierre Vogel, Maris Turks, Claudia Jana Exner

Cyclic stereotriads and stereotetrads of the beta-hydroxy-delta-lactone type, e.g. prelactones B and E, common in polyketides and polypropionates, are prepared via SO2-induced oxyallylations of enoxysilanes with (1E,3Z)-1-(1-phenylethoxy)penta-1,3-dien-3-y ...

2011

Synthesis and Applications of Silyl 2-Methylprop-2-ene-1-sulfinates in Preparative Silylation and GC-Derivatization Reactions of Polyols and Carbohydrates

Pierre Vogel, Maris Turks, Dean Markovic

Trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, and triisopropylsilyl 2-methylprop-2-ene-1-sulfinates were prepared through (CuOTf)(2)C6H6-catalyzed sila-ene reactions of the corresponding methallylsilanes with SO2 at 50 degrees C. Sterically hinde ...

Wiley-V C H Verlag Gmbh2016

Synthesis of Optically Active 5-Alkoxy-6-methylcyclohex-2-en-1-ones and 4-Alkoxy-5-methylcyclopent-1-enyl Benzoate

Pierre Vogel, Maris Turks

The reaction of (-)-(1E,3Z)-2-methyl-1-((1S)-1-phenylethoxy)penta-1,3-dien-3-ol benzoate with allyltrimethylsilane in SO,- and in the presence of a catalytic amount of Tf2NTMS gives a silyl sulfinate intermediate that furnishes (-)-(6Z,1'S,4S,5S)-5-methyl- ...

American Chemical Society2009

Concise Synthesis of Complicated Polypropionates through One-Pot Dissymmetrical Two-Directional Chain Elongation

Pierre Vogel, Maris Turks, Claudia Jana Exner, Freddy Fonquerne

Herein, a major breakthrough in a sulfur dioxide-mediated oxyallylation cascade reaction is reported that allows the preparation of complex long-chain polyketide fragments with more than ten stereogenic centers through a carefully designed desymmetrization ...

2011

Umpolung of 1-alkoxy-3-acyloxy-1,3-dienes with sulfur dioxide and its application in polypropionate synthesis

Maris Turks

Under appropriate conditions sulfur dioxide reacts with 1,3-dienes in the hetero-Diels-Alder fashion. In the case of 1-alkoxy-1,3-dienes the 6-alkoxy-3,6-dihydro-1,2-oxatiin-2-oxides (sultines) so-obtained can be ionized in the presence of Lewis or protic ...

EPFL2004

Efficient Asymmetric Synthesis of Long-Chain Polyketides Containing up to Ten Contiguous Stereogenic Centres by Double Chain Elongation

Rosario Scopelliti, Pierre Vogel, Maris Turks

The 2,3-anti-3,4-syn-stereotriad (1Z,2S,3R,4S)-1-ethylidene-2,4-dimethyl-3-[(1S)-1-phenylethoxy]-5-oxopent-1-yl isobutyrate {(-)-8, obtained in a one-pot operation from the trimethylsilyl (Z)-enol ether derived from pentan-3-one and (1E,3Z)-1[(1S)-phenylet ...

2011

The bora-ene reaction of sulfur dioxide and prop-2-ene-1-boronic esters. New route to sulfoxides

Pierre Vogel, Maris Turks

A new one-pot synthesis of sulfoxides is presented. It involves the bora-ene reaction of sulfur dioxide and prop-2-ene-1-boronic esters, giving mixed anhydrides of sulfinic and boric acids. The latter react chemoselectively at the sulfur center with Grigna ...

Elsevier2006

Total Synthesis and Determination of the Absolute Configuration of (-)-Dolabriferol

Pierre Vogel, Maris Turks

Wiley-VCH Verlag GmbH2010