N. Kuznetsov, V. Khrustalev, T. Strelkova
Nov 1, 2014
Citations
0
Influential Citations
2
Citations
Journal
Russian Chemical Bulletin
Abstract
A four-step synthesis of 11-methyl-13-azabicyclo[7.3.1]trideca-3,10-diene, a potential precursor of the ladybugs´ defensive alkaloids precoccinelline and mirrhine, has been accom-plished. Treatment of 4-picoline with 5-hexenyl-1-lithium, triallylborane, and methanol led to the synthesis of trans-6-allyl-2-(hex-5-enyl)-4-methyl-1,2,3,6-tetrahydropyridine, which reacted with triallylborane upon heating to be converted to the cis-isomer. A subsequent cyclization of the cis-isomer of N-Boc derivative via the intramolecular metathesis using Grubbs II and Hoveyda—Grubbs II ruthenium catalysts furnished the target bridged macrobicycle. The structure of its hydrochloride was confirmed by single crystal X-ray diffraction studies. The optimal conditions for the metathesis reaction and the isolation of the macrobicyclic product were selected.