Stereoselective total synthesis of (−)-brevisamide

Stereoselective total synthesis of (−)-brevisamide

The stereoselective total synthesis of (−)-brevisamide, a novel marine cyclic ether alkaloid isolated from dinoflagellate karenia brevis is described. The key steps involved in this synthesis are the Sharpless asymmetric epoxidation and regioselective ring opening of chiral epoxide by Gilman's...

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Veröffentlicht in:Tetrahedron 2013-10, Vol.69 (40), p.8618-8625
Hauptverfasser: Yadav, J.S., Reddy, N. Mallikarjuna, Rahman, Md. Ataur, Prasad, A.R., Reddy, B.V. Subba
Format: Artikel
Sprache:eng
Schlagworte:
Alkaloids
Asymmetry
Dinoflagellates
Ethers
Gilman's reaction
Horner–Wadsworth–Emmons reaction
Marine
Ring opening
Sharpless asymmetric epoxidation
SN2 cyclisation
Synthesis (chemistry)
TEMPO-BIAB oxidation
Tetrahedrons
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Zusammenfassung:The stereoselective total synthesis of (−)-brevisamide, a novel marine cyclic ether alkaloid isolated from dinoflagellate karenia brevis is described. The key steps involved in this synthesis are the Sharpless asymmetric epoxidation and regioselective ring opening of chiral epoxide by Gilman's reagent. The tetrahydropyran core has been constructed by an intramolecular SN2 cyclisation. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.07.072