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: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 45, No. 1, 1997, pp.147-156
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7655
INOC Reaction in Alkaloid Synthesis — Stereocontrolled Formal Total Synthesis of (+)-Pumiliotoxin C

Masahiro Toyota,* Takanobu Asoh, and Keiichiro Fukumoto

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

A formal total synthesis of (+)-pumiliotoxin C (1), the antipode of the arrow poison frog toxin, starting from the chirally homogeneous (1’S, 6’S)-2-(6’-benzyloxymethyl-2’-cyclohexyl)ethanol (2) is described. The synthesis features the intramolecular nitrile oxide cycloaddition (INOC) reaction of the nitro olefin (5) to furnish the isoxazoline (6).