Intramolecular cyclization by catalytic hydrogenation of 3β-acetoxy-16-picolinylidene-5-androsten-17-one (IV) (80° and 50-60 atm of hydrogen pressure over Pd/C as catalyst) gives rise to the formation of two cyclic products, namely, 5′,6′,7′,8′-tetrahydro-2′αH-3′αH-9′αH-3β-acetoxy-androst-5-eno [16.17-b]indolizine (VII) and its 9′βH-isomer (VIII), in a total yield of over 80%, the ratio of the two isomers being 3:1. The cyclized products have structures similar to naturally occuring alkaloid solanidine. A mechanism is proposed for the cyclization.
TY - JOUR
AU - Stefanović, Milutin
AU - Mićović, Ivan V.
AU - Jeremić, Dragoslav
AU - Miljković, Dušan
PY - 1970
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4593
AB - Intramolecular cyclization by catalytic hydrogenation of 3β-acetoxy-16-picolinylidene-5-androsten-17-one (IV) (80° and 50-60 atm of hydrogen pressure over Pd/C as catalyst) gives rise to the formation of two cyclic products, namely, 5′,6′,7′,8′-tetrahydro-2′αH-3′αH-9′αH-3β-acetoxy-androst-5-eno [16.17-b]indolizine (VII) and its 9′βH-isomer (VIII), in a total yield of over 80%, the ratio of the two isomers being 3:1. The cyclized products have structures similar to naturally occuring alkaloid solanidine. A mechanism is proposed for the cyclization.
PB - Elsevier
T2 - Tetrahedron
T1 - Intramolecular cyclization of 3β-acetoxy-16-picolinylidene-5-androsten-17-one by catalytic hydrogenation
VL - 26
IS - 11
SP - 2609
EP - 2617
DO - 10.1016/S0040-4020(01)92835-2
ER -
@article{
author = "Stefanović, Milutin and Mićović, Ivan V. and Jeremić, Dragoslav and Miljković, Dušan",
year = "1970",
abstract = "Intramolecular cyclization by catalytic hydrogenation of 3β-acetoxy-16-picolinylidene-5-androsten-17-one (IV) (80° and 50-60 atm of hydrogen pressure over Pd/C as catalyst) gives rise to the formation of two cyclic products, namely, 5′,6′,7′,8′-tetrahydro-2′αH-3′αH-9′αH-3β-acetoxy-androst-5-eno [16.17-b]indolizine (VII) and its 9′βH-isomer (VIII), in a total yield of over 80%, the ratio of the two isomers being 3:1. The cyclized products have structures similar to naturally occuring alkaloid solanidine. A mechanism is proposed for the cyclization.",
publisher = "Elsevier",
journal = "Tetrahedron",
title = "Intramolecular cyclization of 3β-acetoxy-16-picolinylidene-5-androsten-17-one by catalytic hydrogenation",
volume = "26",
number = "11",
pages = "2609-2617",
doi = "10.1016/S0040-4020(01)92835-2"
}
Stefanović, M., Mićović, I. V., Jeremić, D.,& Miljković, D.. (1970). Intramolecular cyclization of 3β-acetoxy-16-picolinylidene-5-androsten-17-one by catalytic hydrogenation. in Tetrahedron
Elsevier., 26(11), 2609-2617.
https://doi.org/10.1016/S0040-4020(01)92835-2
Stefanović M, Mićović IV, Jeremić D, Miljković D. Intramolecular cyclization of 3β-acetoxy-16-picolinylidene-5-androsten-17-one by catalytic hydrogenation. in Tetrahedron. 1970;26(11):2609-2617.
doi:10.1016/S0040-4020(01)92835-2 .
Stefanović, Milutin, Mićović, Ivan V., Jeremić, Dragoslav, Miljković, Dušan, "Intramolecular cyclization of 3β-acetoxy-16-picolinylidene-5-androsten-17-one by catalytic hydrogenation" in Tetrahedron, 26, no. 11 (1970):2609-2617,
https://doi.org/10.1016/S0040-4020(01)92835-2 . .
