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Sulfur dioxide-mediated syntheses of polyfunctional alkenes and (E,Z)- and (E,E)-2,4-dien-1-ones

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

Pierre Vogel, Rosario Scopelliti, 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

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The stereoselective synthesis of new 3,4-dihydroxypyrrolidine derivatives starting from D-mannose, D-ribose and L-fucose is presented. Two synthetic strategies employing organometallic addition to hemiacetalic sugars followed by selective nucleophilic disp ...

2009

Functional groups are prerequisites for the assembly of building blocks to more elaborate structures for research work in the life sciences field. Functionalization can be most conveniently and efficaciously accomplished by generating an organometallic der ...

American Chemical Society2009

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In the presence of a Lewis or protic acid and at low temperature, 1,3-dioxy-1,3-dienes add to sulfur dioxide generating zwitterionic intermediates that can react with carbon nucleophiles such as allylsilanes. After a retro-ene elimination of SO2, valuable ...

2004

The conversion of 2,2-difluoro-1,3-benzodioxole, an exceptionally acidic arene, via a 4-lithiated intermediate into more than three dozen new derivs. was conceived as a case study. The lithiated species was trapped by C0-electrophiles (4-toluenesulfonyl az ...

2003

The Bright Future of Stereoselective Synthesis of Coordination Compounds

Transfer of chirality during the build-up of molecules has been applied innumerable times in organic chemistry since the end of the 19th century, when it was introduced in the so-called asymmetric synthesis by E. Fischer. Although analogous reactions were ...

2000

An asymmetric total synthesis of sanjoinine G1

Jieping Zhu

A convergent total synthesis of sanjoinine G1 (I), a 14-membered cyclopeptide alkaloid was described. Formation of aryl alkyl ether bond with concomitant construction of macrocycle by way of an intramol. SNAr reaction was the key step in this synthesis. On ...

1999

Triacetate of 7-oxabicyclo[2.2.1]hept-5-ene-1,2-exo,3-exo-trimethanol was converted selectively into (1RS,2SR,5RS,6RS)-4,5,6-tris(acetoxymethyl)-2-bromocyclohex-3-en-1-ol (4) or into (1RS,2SR,5RS,6RS)-5,6-bis(acetoxymethyl)-2-bromo-4-bromomethylcyclohex-3 ...

1998

'Naked sugars of the second generation': Asymmetric synthesis of long-chain polypropionates and analogues starting with acetone

Pierre Vogel

Homochiral Diels-Alder adduct of 2,4-dimethylfuran to 1-cyanovinyl (1'R)- or (1'S)-camphanate are transformed readily into polypropionate fragments containing four or five contiguous stereogenic centres. They can be condensed via cross-aldolizations to lit ...

1996

Michael addition of (-)-(1S,5R,6R,7S)-6,7-bis(methoxymethoxy)-2,8-dioxabicyclo[3.2.1]-octan- 3-one lithium enolate to (+)-(1R,4S,5S,6S)-5-benzeneselenyl-6-chloro-3-methylidene-7-oxabicyclo[2 .2.1]heptan-2-one gives a single adduct with highstereoselectivit ...

1996