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Iterative synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin

โœ Scribed by Yuji Mori; Toyohisa Takase; Ryoji Noyori

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
430 KB
Volume
44
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A stereocontrolled linear synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin, diarrhetic shellfish toxins, is described. Iterative application of a tetrahydropyran synthesis by reaction of the alkylation of a sulfonyl-stabilized oxiranyl anion followed by 6-endo cyclization of a 4,5-epoxy alcohol led to the synthesis of the trans-fused hexacyclic ether system, and the seven-membered E ring was constructed by ring expansion reaction.

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