Search

Your search keyword '"Jeffrey L. C. Wright"' showing total 5 results
Start Over Author "Jeffrey L. C. Wright" Journal organic letters
5 results on '"Jeffrey L. C. Wright"'

1. Brevisamide: An Unprecedented Monocyclic Ether Alkaloid from the Dinoflagellate Karenia brevis That Provides a Potential Model for Ladder-Frame Initiation

Author

Daniel G. Baden, Masayuki Satake, Ryan M. Van Wagoner, Jeffrey L. C. Wright, and Andrea J. Bourdelais

Subjects
Magnetic Resonance Spectroscopy, Stereochemistry, Molecular Conformation, Ether, Biochemistry, Mass Spectrometry, Article, chemistry.chemical_compound, Alkaloids, Animals, Spectral analysis, Thiopental, Physical and Theoretical Chemistry, Pyrans, biology, Chemistry, Alkaloid, Organic Chemistry, Dinoflagellate, Brevisamide, Reference Standards, biology.organism_classification, Cyclic ether, Dinoflagellida, Fatty Acids, Unsaturated, Karenia brevis, Ethers
Abstract

The dinoflagellate Karenia brevis is known for the production of brevetoxins, a family of polycyclic ether toxins, as well as their antagonist brevenal. Further examination of organic extracts of K. brevis has uncovered yet another unprecedented cyclic ether alkaloid named brevisamide. This report describes the structure elucidation of brevisamide based on detailed MS and NMR spectral analysis, and the importance of this new compound in shedding light on the biogenesis of fused polyethers is discussed.

Published
2008
Full Text
View/download PDF

2. Total synthesis of (-)-brevisin: a concise synthesis of a new marine polycyclic ether

Author

Jeffrey L. C. Wright, Daniel G. Baden, Ryosuke Tsutsumi, Kazuo Tachibana, Takefumi Kuranaga, Masayuki Satake, and Naohito Ohtani

Subjects
Marine biology, Molecular Structure, Longest linear sequence, Organic Chemistry, Total synthesis, Ether, Stereoisomerism, Marine Biology, Biochemistry, Combinatorial chemistry, Article, chemistry.chemical_compound, chemistry, Ethers, Cyclic, Dinoflagellida, Organic chemistry, Molecule, Polycyclic Compounds, Physical and Theoretical Chemistry
Abstract

The first and highly efficient total synthesis of (−)-brevisin has been achieved. The title compound was synthesized in only 29 steps (longest linear sequence) from commercially available starting materials. The synthesis provided over 70 mg of a marine polycyclic ether compound.

Published
2011

3. Total synthesis and structural confirmation of brevisamide, a new marine cyclic ether alkaloid from the dinoflagellate Karenia brevis

Author

Daniel G. Baden, Masayuki Satake, Takefumi Kuranaga, Tomohiro Shirai, Kazuo Tachibana, and Jeffrey L. C. Wright

Subjects
biology, Chemistry, Stereochemistry, Alkaloid, Organic Chemistry, Dinoflagellate, Molecular Conformation, Total synthesis, Brevisamide, Ether, Stereoisomerism, biology.organism_classification, Biochemistry, chemistry.chemical_compound, Alkaloids, Cyclic ether, Side chain, Dinoflagellida, Fatty Acids, Unsaturated, Animals, Karenia brevis, Physical and Theoretical Chemistry, Pyrans
Abstract

The first total synthesis of brevisamide (1) has been accomplished in 21 linear steps starting from cis-but-2-ene-1,4-diol. A synthetic highlight is the Suzuki−Miyaura coupling between an ether ring fragment and a dienol side chain. This result confirmed the structure of 1 isolated from the dinoflagellate Karenia brevis.

Published
2008

Catalog

Books, media, physical & digital resources
See catalog results