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

Communication | Regular issue | Vol 38, No. 11, 1994, pp.2383-2388
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6869
Stereoselective Conversion of L-Quebrachitol into a Novel Hydroxylated Caprolactam: Total Synthesis of Bengamide B

Noritaka Chida,* Takahiko Tobe, Katsuyuki Murai, Kaori Yamazaki, and Seiichiro Ogawa*

*Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku, Yokohama 223-8522, Japan


The stereoselective synthesis of the novel marine natural product, bengamide B (1), starting from L-quebrachitol (3) is described. The hydroxylated caprolactam portion (2a) in 1 was prepared from (+)-conduramine derivative (7), whose amino functionality was introduced stereoselectively by means of palladium-catalyzed azidation of a chiral cyclohexene (6) derived from 3.