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Intramolecular cyclization of 3β-acetoxy-16-picolinylidene-5-androsten-17-one by catalytic hydrogenation

Authorized Users Only
1970
Authors
Stefanović, Milutin
Mićović, Ivan V.
Jeremić, Dragoslav
Miljković, Dušan
Article (Published version)
Metadata
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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.
Keywords:
catalytic hydrogenation / Intramolecular cyclization / hydrogen pressure / isomer / cyclization
Source:
Tetrahedron, 1970, 26, 11, 2609-2617
Publisher:
  • Elsevier

DOI: 10.1016/S0040-4020(01)92835-2

ISSN: 0040-4020; 1464-5416

Scopus: 2-s2.0-0014799380
[ Google Scholar ]
6
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/4593
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
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 . .

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