Results 71 to 80 of about 155 (104)

Stereoselective Synthesis of the C1–C29 Part of Amphidinol 3

The Journal of Organic Chemistry, 2015
Stereoselective synthesis of the C1-C29 part of amphidinol 3 (AM3) was achieved. The C1-C20 part was assembled from three building blocks via regioselective cross metathesis to form the C4-C5 double bond and addition of an alkenyllithium and a lithium acetylide to two Weinreb amides followed by asymmetric reduction to form the C9-C10 and C14-C15 bonds,
Takeshi, Tsuruda, Makoto, Ebine, Aya, Umeda, Tohru, Oishi   +3 more
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Diastereoselective synthesis of the C17–C30 fragment of amphidinol 3

Organic & Biomolecular Chemistry, 2012
The diastereoselective synthesis of the C17-C30 fragment of amphidinol 3 (AM3) 1 was achieved from the enantio-enriched aldehyde 20, Weinreb amide 14 and 2-bromo-3-(trimethylsilyl)propene, which was used as a bifunctional conjunctive reagent. The absolute configuration of the stereogenic centers, in both aldehyde 20 and Weinreb amide 14, were ...
Rival, Nicolas, Hazelard, Damien, Hanquet, Gilles, Kreuzer, Thomas, Bensoussan, Charlelie, Reymond, Sébastien, Cossy, Janine, Colobert, Françoise   +7 more
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Structures of new amphidinols with truncated polyhydroxyl chain and their membrane-permeabilizing activities

Bioorganic and 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.
Michio Murata, Tohru Oishi, Nobuaki Matsumori   +2 more
exaly   +3 more sources

Structure of Membrane-Bound Amphidinol 3 in Isotropic Small Bicelles

Organic Letters, 2008
Amphidinol 3 (AM3) exhibits a potent membrane permeabilizing activity by forming pores in biological membranes. We examined the conformation and location of AM3 using isotropic bicelles, a more natural membrane model than micelles. The results show that AM3 takes turn structures at the two tetrahydropyran rings.
Toshihiro, Houdai, Nobuaki, Matsumori, Michio, Murata   +2 more
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Synthesis and Structure Revision of the C43–C67 Part of Amphidinol 3

Organic Letters, 2013
Stereoselective synthesis of the C43-C67 part of amphidinol 3 (AM3) and its C51-epimer was achieved starting from a common intermediate corresponding to the tetrahydropyran moiety of AM3, via asymmetric oxidations and Julia-Kocienski olefination. By comparing NMR data of the synthetic specimens with those of AM3, the absolute configuration at C51 of ...
Makoto, Ebine, Mitsunori, Kanemoto, Yoshiyuki, Manabe, Yosuke, Konno, Ken, Sakai, Nobuaki, Matsumori, Michio, Murata, Tohru, Oishi   +7 more
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Synthesis of the C(43)−C(67) Fragment of Amphidinol 3

Organic Letters, 2005
[reaction: see text] A synthesis of the C(43)-C(67) fragment of amphidinol 3 (AM3) has been accomplished by a route that features the use of a double allylboration reaction for synthesis of 1,5-diol 4b, which serves as a precursor to dihydropyran 11.
Jacqueline D, Hicks, Eric M, Flamme, William R, Roush   +2 more
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Isolation, structural determination and synthetic approaches toward amphidinol 3

Natural Product Reports, 2014
This review highlights the isolation and the structural determination of amphidinol 3 (AM3), as well as the synthetic efforts to its preparation. The mechanism of action of AM3 will not be developed herein.
Bensoussan, Charlélie, Rival, Nicolas, Hanquet, Gilles, Colobert, Françoise, Reymond, Sébastien, Cossy, Janine   +5 more
openaire   +2 more sources

Direct and Stereospecific Interaction of Amphidinol 3 with Sterol in Lipid Bilayers

Biochemistry, 2014
Amphidinol 3 (AM3), a polyhydroxy-polyene metabolite from the dinoflagellate Amphidinium klebsii, possesses potent antifungal activity. Although AM3 permeabilizes phospholipid membranes only in the presence of sterol, the detailed molecular basis by which AM3 recognizes sterols in membranes remains unknown.
Rafael Atillo, Espiritu, Nobuaki, Matsumori, Masashi, Tsuda, Michio, Murata   +3 more
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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, Hanquet, Gilles, Bensoussan, Charlelie, Reymond, Sébastien, Cossy, Janine, Colobert, Françoise   +5 more
openaire   +1 more source

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 ...
Lesley Rhodes, Masayuki Satake, Michio Murata   +2 more
exaly   +2 more sources