Results 101 to 110 of about 206 (130)

Total Synthesis of Amphidinol 3: A General Strategy for Synthesizing Amphidinol Analogues and Structure–Activity Relationship Study

Journal of the American Chemical Society, 2020
Amphidinol 3 (AM3) is a potent antifungal produced by the dinoflagellate Amphidinium klebsii. It was difficult to determine the absolute configuration of AM3 by using the scarce natural product due to the presence of numerous stereogenic centers on the acyclic carbon chain.
Yuma Wakamiya, Makoto Ebine, Nobuaki Matsumori, Tohru Oishi   +3 more
openaire   +2 more sources

Synthesis of the C31—C67 Fragment of Amphidinol 3.

ChemInform, 2006
AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.
Javier, de Vicente, John R, Huckins, Scott D, Rychnovsky   +2 more
openaire   +2 more sources

Confirmation of the Absolute Configuration at C45 of Amphidinol 3

Journal of Natural Products, 2012
Amphidinol 3 (AM3), a membrane-active agent isolated from the dinoflagellate Amphidinium klebsii, consists of a long carbon chain containing 25 stereogenic centers. Although the absolute configuration of AM3 was determined by extensive NMR analysis and degradation of the natural product, the partial structure corresponding to the tetrahydropyran ring ...
Yoshiyuki, Manabe, Makoto, Ebine, Nobuaki, Matsumori, Michio, Murata, Tohru, Oishi   +4 more
openaire   +2 more sources

Synthesis of highly substituted 2,6-anti-configured tetrahydropyrans. First steps towards an efficient access to amphidinol 3 ring system

Tetrahedron Letters, 2005
Highly functionalised and polysubstituted tetrahydropyrans, akin to the middle core of the amphidinols, can be efficiently synthesised, with full stereocontrol and in good yields, using as key steps an anti-allylation reaction coupled with an ...
Marko, Istvan, Bryans, J, Dubost, C
exaly   +2 more sources

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 ...
Nicolas, Rival, Damien, Hazelard, Gilles, Hanquet, Thomas, Kreuzer, Charlelie, Bensoussan, Sébastien, Reymond, Janine, Cossy, Françoise, Colobert   +7 more
openaire   +2 more sources

Production of Amphidinols and Other Bioproducts of Interest by the Marine Microalga Amphidinium carterae Unraveled by Nuclear Magnetic Resonance Metabolomics Approach Coupled to Multivariate Data Analysis

Journal of Agricultural and Food Chemistry, 2019
This study assessed the feasibility of an NMR metabolomics approach coupled to multivariate data analysis to monitor the naturally present or stresses-elicited metabolites from a long-term (>170 days) culture of the dinoflagellate marine microalgae ...
Ana Cristina Abreu, A Molina-Miras, L López-Rosales   +2 more
exaly   +3 more sources

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
openaire   +2 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
openaire   +2 more sources

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
openaire   +2 more sources

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
openaire   +2 more sources