Practical route to the left wing of CTX1B and total syntheses of CTX1B and 54-deoxyCTX1B.

Abstract

Ciguatoxins, the principal causative agents of ciguatera seafood poisoning, are extremely large polycyclic ethers. We report herein a reliable route for constructing the left wing of CTX1B, which possesses the acid/base/oxidant-sensitive bisallylic ether moiety, by a 6-exo radical cyclization/ring-closing metathesis strategy. This new route enabled us to achieve the second-generation total synthesis of CTX1B and the first synthesis of 54-deoxyCTX1B.

• Authors: Shuji Yamashita, Katsutoshi Takeuchi, Takuya Koyama, Masayuki Inoue, Yujiro Hayashi, Masahiro Hirama
• Journal: Chemistry (Weinheim an der Bergstrasse, Germany) (Chemistry) Vol. 21 Issue 6 Pg. 2621-8 (Feb 02 2015) ISSN: 1521-3765 [Electronic] Germany
• PMID: 25529606 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Chemical References

• Ethers
• Free Radicals
• ciguatoxin 1B (CTX 1B)
• Ciguatoxins
• Safrole
• sulfoxide

Topics

• Ciguatoxins (chemical synthesis, chemistry)
• Cyclization
• Ethers (chemistry)
• Free Radicals (chemistry)
• Quantum Theory
• Safrole (analogs & derivatives, chemistry)
• Stereoisomerism