A. M. Agafontsev, T. V. Rybalova, Yu. V. Gatilov, A. V. Tkachev, “First stereoselective cyclisation in the cembrane series: X-ray structure of (+)-(4R,8R,11S,12E,14S,16R)-11-isopropyl-4,8,14-trimethyl-14-morpholin-4-yl-3-oxa-2-azatricyclo[6.6.2.04,16]hexadeca-1,12-diene”, Mendeleev Commun., 2009, Volume 19, Issue 5,Pages 246

This article is cited in 2 papers

First stereoselective cyclisation in the cembrane series: X-ray structure of (+)-(4R,8R,11S,12E,14S,16R)-11-isopropyl-4,8,14-trimethyl-14-morpholin-4-yl-3-oxa-2-azatricyclo[6.6.2.0^4,16]hexadeca-1,12-diene

A. M. Agafontsev^a, T. V. Rybalova^a, Yu. V. Gatilov^a, A. V. Tkachev^ab

^a N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russian Federation
^b Department of Natural Sciences, Novosibirsk State University, Novosibirsk, Russian Federation

Abstract: A simple synthetic derivative of natural diterpene cembrene [(1S,2E,4S,7E,11E)-4-morpholin-4-ylcembra-2,7,11-trien-5-one E-oxime] was found to be highly sensitive to acids (sulfuric and trifluoroacetic), and it is transformed under acidic conditions to atricyclic bridged system with the 5,6-dihydro-4H-1,2-oxazine moiety.

Keywords: cembrene, diterpene, cyclisation, stereoselective, X-ray.

Language: English

DOI: 10.1016/j.mencom.2009.09.003