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 94, No. 2, 2017, pp.286-296
Published online, 24th January, 2017
DOI: 10.3987/COM-16-13631
Synthesis of (-)-Isosolenopsin Using Diastereoselective Aminopalladation

Yukiko Takemoto, Yasunao Hattori, and Hidefumi Makabe*

*Sciences of Functional Foods, Graduate School of Agriculture, Shinshu University, 8304 Minamiminowa-mura, Kamiina-gun, Nagano 399-4598, Japan

Abstract

Concise synthesis of (-)-isosolenopsin, a piperidine alkaloid isolated from the fire ants (Solenopsis) was achieved. 2,6-Disubstituted piperidine ring of (-)-isosolenopsin was constructed using diastereoselective aminopalladation. Chain elongation using Grubbs 2nd catalyst followed by reduction of double bond and deprotection of the Boc group afforded (-)-isosolenopsin.