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 43, No. 10, 1996, pp.2229-2248
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7562
Total Synthesis of (8'R)- and (8'S)-Corossoline

Hidefumi Makabe, Hisahide Tanimoto, Akira Tanaka, and Takayuki Oritani

*Division of Environmental Bioremediation, Graduate School of Agricultural Science, Tohoku University, 1-1 Tsutsumidori-Amamiya, Aoba-ku, Sendai 981-8555, Japan

Abstract

A convergent stereoselective total synthesis of (8’R)- and (8’S)-corossoline (1) has been performed via a multi-step process. Comparison of the mp, [α]D, ir and nmr data of both synthetic materials with those reported for natural corossoline did not allow for the strict deterimination of the donfiguration at the C-8’ hydroxyl group of 1. However, a slight chemical shift difference at the C-8’ methine proton was observrd in the 1H-nmr spectra of the corresponding tris-MTPA esters of synthetic (8’R)- and (8’S)-1, indicating that if the tris-MTPA ester of natural 1 is available, the stereochemistry at the C-8’ hydroxyl group of corossoline will be established.