Home / Publications / 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

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

Alexander Mikhailovich Agafontsev 1
Alexander Mikhailovich Agafontsev
, 
Tatyana Valeryevna Rybalova 1
Tatyana Valeryevna Rybalova
, 
Yuriy Vasil'evich Gatilov 1
Yuriy Vasil'evich Gatilov
, 
Alexey Vasil'evich Tkachev 1, 2
Alexey Vasil'evich Tkachev
10.1016/j.mencom.2009.09.003
Published 2009-09-15
Communication , Volume 19, Issue 5, 246-247
2
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Agafontsev A. M. et al. 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 Communications. 2009. Vol. 19. No. 5. pp. 246-247.
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Agafontsev A. M., Rybalova T. V., Gatilov Y. V., Tkachev A. V. 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 Communications. 2009. Vol. 19. No. 5. pp. 246-247.
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TY - JOUR
DO - 10.1016/j.mencom.2009.09.003
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2009.09.003
TI - 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
T2 - Mendeleev Communications
AU - Agafontsev, Alexander Mikhailovich
AU - Rybalova, Tatyana Valeryevna
AU - Gatilov, Yuriy Vasil'evich
AU - Tkachev, Alexey Vasil'evich
PY - 2009
DA - 2009/09/15
PB - Mendeleev Communications
SP - 246-247
IS - 5
VL - 19
ER -
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@article{2009_Agafontsev,
author = {Alexander Mikhailovich Agafontsev and Tatyana Valeryevna Rybalova and Yuriy Vasil'evich Gatilov and Alexey Vasil'evich Tkachev},
title = {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},
journal = {Mendeleev Communications},
year = {2009},
volume = {19},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2009.09.003},
number = {5},
pages = {246--247},
doi = {10.1016/j.mencom.2009.09.003}
}
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Agafontsev, Alexander Mikhailovich, et al. “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 Communications, vol. 19, no. 5, Sep. 2009, pp. 246-247. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2009.09.003.

Keywords

cembrene
cyclisation
Diterpene
stereoselective
X-ray

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.

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