Results 81 to 90 of about 175 (106)
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Diastereoselective synthesis of the C14–C29 fragment of amphidinol 3

Organic & Biomolecular Chemistry, 2013
An efficient stereoselective synthesis of the C14–C29 fragment highlighting a coupling reaction between a 1,3-dithiane derivative and an α-branched aldehyde was realized. This highly convergent synthesis involved two chiral pools, L-malic acid and (+)-camphorsulfonic acid, which are the starting compounds to control the six stereogenic centers present ...
Rival, Nicolas   +5 more
openaire   +1 more source

Stereoselective Synthesis of the C31−C40/C43−C52 Unit of Amphidinol 3

The Journal of Organic Chemistry, 2009
A concise synthesis of a tetrahydropyran ring system corresponding to the C31-C40 and C43-C52 units of amphidinol 3 is described. Successive chemoselective reactions, i.e., cross-metathesis to differentiate the iodoolefin from the terminal olefin and Sharpless asymmetric dihydroxylation on the resulting E-olefin, resulted in expeditious synthesis of an
Mitsunori, Kanemoto   +2 more
openaire   +2 more sources

Development of an Access Route to the C31−C52 Central Core of Amphidinol 3

Organic Letters, 2007
[reaction: see text] An asymmetric synthesis of the heavily oxygenated inner sector of amphidinol 3 constituted of C31-C52 is described. The successful pathway highlights construction of the pair of identical tetrahydropyran subunits from a common intermediate.
Matthew W, Bedore   +2 more
openaire   +2 more sources

The cytotoxicity of lingshuiol: A comparative study with amphidinol 2 on membrane permeabilizing activities

Toxicon, 2007
The cytotoxicity of lingshuiol, a novel polyhydroxy compound with a linear carbon-chain isolated from the cultured marine dinoflagellate Amphidinium sp., and that of amphidinol 2 (AM2) was compared with hepatocytes. Both lingshuiol and AM2 were toxic to primary rat hepatocytes with IC(50) values of 0.21 and 6.4muM, respectively.
Xin-Ming, Qi   +5 more
openaire   +2 more sources

Structures of new amphidinols with truncated polyhydroxyl chain and their membrane-permeabilizing activities

Bioorganic & Medicinal Chemistry, 2006
Two new homologues of amphidinols (AM14 and AM15) were isolated from the cultured dinoflagellate Amphidinium klebsii. The structures were elucidated on the basis of 2D NMR and collision-induced dissociation MS/MS and turned out to be closely related homologues of AM7.
Nagy, Morsy   +8 more
openaire   +2 more sources

Diastereoselective synthesis of the C14–C29 fragment of amphidinol.

Organic & biomolecular chemistry, 2014
An efficient stereoselective synthesis of the C14–C29 fragment highlighting a coupling reaction between a 1,3-dithiane derivative and an α-branched aldehyde was realized. This highly convergent synthesis involved two chiral pools, L-malic acid and (+)-camphorsulfonic acid, which are the starting compounds to control the six stereogenic centers present ...
Nicolas, Rival   +5 more
openaire   +1 more source

Structure and Biosynthesis of Amphidinol 17, a Hemolytic Compound from Amphidinium carterae

Journal of Natural Products, 2010
Amphidinol 17 (AM17; 1), a novel amphidinol, has been isolated from a Bahamas strain of Amphidinium carterae. This new congener contains the signature hairpin region and a Delta(6) polyene arm, whereas the polyol arm is distinct from those of other amphidinols.
Yanhui, Meng   +4 more
openaire   +2 more sources

Acetate labeling patterns of dinoflagellate polyketides, amphidinols 2, 3 and 4

Tetrahedron, 2001
Abstract Amphidinols, which are polyketide metabolites chiefly comprising a long linear chain with polyhydroxyl groups and polyolefins, are produced by marine dinoflagellates Amphidinium carterae and A. klebsii. The acetate incorporation experiments of amphidinols 2, 3 and 4 revealed that they are built up with five regular C2-elongation sequences ...
Toshihiro Houdai   +6 more
openaire   +1 more source

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