Sulfonyl-stabilized oxiranyllithium-based approach to polycyclic ethers. Convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin.

Abstract

Convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin, marine polycyclic ether toxins causative of diarrheic shellfish poisoning, has been accomplished. The A-ring fragment was constructed by coupling of an appropriately functionalized sulfonyl-stabilized oxiranyl anion and a triflate prepared from an erythritol derivative. An iterative protocol of the oxiranyl anion strategy was also applied for the construction of the DEF-ring fragment. The triflate derivatives of the A-ring and the DEF-ring fragments were connected with lithium acetylide. The resulting acetylene derivative was further transformed into the hexacyclic ABCDEF fragment via oxidation of the acetylene unit to 1,2-diketone, double methyl acetal formation, and reductive etherification.

• Authors: Yuji Mori, Kouichi Nogami, Hiasafumi Hayashi, Ryoji Noyori
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 68 Issue 23 Pg. 9050-60 (Nov 14 2003) ISSN: 0022-3263 [Print] United States
• PMID: 14604380 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Ethers
• Ethers, Cyclic
• Mollusk Venoms
• Oxocins
• adriatoxin
• Lithium
• yessotoxin

Topics

• Ethers (chemical synthesis, chemistry)
• Ethers, Cyclic (chemical synthesis, chemistry)
• Lithium (chemistry)
• Molecular Structure
• Mollusk Venoms
• Oxocins (chemical synthesis, chemistry)
• Spectrum Analysis