Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Special issue | Vol 82, No. 1, 2010, pp.761-774
Published online, 27th July, 2010
DOI: 10.3987/COM-10-S(E)61
Stereoselective Synthesis of Caribbean Ciguatoxin M-Ring Using [2+2] Photocyclization

Shuji Yamashita,* Naoya Iijima, Takahiro Shida, and Masahiro Hirama*

*Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan


Ciguatoxins, the principal causative toxins of ciguatera seafood poisoning, are potent toxic polycyclic ethers. We report herein a stereoselective synthesis of the seven-membered M-ring moiety of Caribbean ciguatoxin C-CTX-1. The key features of the synthesis are the photo-induced [2+2] electrocyclization and enzymatic asymmetric hydrolysis to construct the congested oxepane ring.