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

Short Paper | Special issue | Vol 84, No. 2, 2012, pp.1227-1233
Published online, 3rd June, 2011
DOI: 10.3987/COM-11-S(P)14
Formal Synthesis of (-)-Clavepictine A and (+)-Clavepictine B from a Sulfinimine (N-Sulfinylimine)-Derived Chiral Building Block

Franklin A. Davis* and He Xu

*Department of Chemistry, Temple University, 1901 N. 13th Street, Philadelphia, PA 19122, U.S.A.

Abstract

The sulfinimine-derived chiral building block trans-2,6-disubstituted 1,2,5,6-tetrahydropiperidine (+)-5 was employed in a concise formal asymmetric synthesis of the cytotoxic marine alkaloids clavepictines (-)-A and (+)-B (1a and 1b). This synthesis is highlighted by a highly diastereoselective hydroboration-oxidation reaction to install the C-3 hydroxyl group.