Annulations of allene-substituted proline derivatives promoted by transition metals have been investigated as a general way to access bicyclic structures with a bridgehead nitrogen. Two processes, Pd- and Ag-catalysed cyclisations, have been employed complementary to control the substitution pattern of the product. The investigated methodologies afforded the bicyclic derivatives in comparable yields, while Ag-catalysis showed higher level of diastereoselectivity. Both processes have been utilized in the synthesis of naturally occurring pyrroles longamide B, stylisine D and their derivatives.
Keywords:
Ag-catalysis / Annulation / Longamide B / Pd-catalysis / Stylisine D
Source:
European Journal of Organic Chemistry, 2020, 2020, 3, 295-305
TY - JOUR
AU - Jovanović, Miloš
AU - Petković, Miloš
AU - Jovanović, Predrag
AU - Simić, Milena
AU - Tasić, Gordana
AU - Erić, Slavica
AU - Savić, Vladimir
PY - 2020
UR - http://farfar.pharmacy.bg.ac.rs/handle/123456789/3481
AB - Annulations of allene-substituted proline derivatives promoted by transition metals have been investigated as a general way to access bicyclic structures with a bridgehead nitrogen. Two processes, Pd- and Ag-catalysed cyclisations, have been employed complementary to control the substitution pattern of the product. The investigated methodologies afforded the bicyclic derivatives in comparable yields, while Ag-catalysis showed higher level of diastereoselectivity. Both processes have been utilized in the synthesis of naturally occurring pyrroles longamide B, stylisine D and their derivatives.
PB - Wiley-Blackwell
T2 - European Journal of Organic Chemistry
T1 - Proline Derived Bicyclic Derivatives through Metal Catalysed Cyclisations of Allenes: Synthesis of Longamide B, Stylisine D and their Derivatives
VL - 2020
IS - 3
SP - 295
EP - 305
DO - 10.1002/ejoc.201901554
ER -
@article{
author = "Jovanović, Miloš and Petković, Miloš and Jovanović, Predrag and Simić, Milena and Tasić, Gordana and Erić, Slavica and Savić, Vladimir",
year = "2020",
url = "http://farfar.pharmacy.bg.ac.rs/handle/123456789/3481",
abstract = "Annulations of allene-substituted proline derivatives promoted by transition metals have been investigated as a general way to access bicyclic structures with a bridgehead nitrogen. Two processes, Pd- and Ag-catalysed cyclisations, have been employed complementary to control the substitution pattern of the product. The investigated methodologies afforded the bicyclic derivatives in comparable yields, while Ag-catalysis showed higher level of diastereoselectivity. Both processes have been utilized in the synthesis of naturally occurring pyrroles longamide B, stylisine D and their derivatives.",
publisher = "Wiley-Blackwell",
journal = "European Journal of Organic Chemistry",
title = "Proline Derived Bicyclic Derivatives through Metal Catalysed Cyclisations of Allenes: Synthesis of Longamide B, Stylisine D and their Derivatives",
volume = "2020",
number = "3",
pages = "295-305",
doi = "10.1002/ejoc.201901554"
}
Jovanović M, Petković M, Jovanović P, Simić M, Tasić G, Erić S, Savić V. Proline Derived Bicyclic Derivatives through Metal Catalysed Cyclisations of Allenes: Synthesis of Longamide B, Stylisine D and their Derivatives. European Journal of Organic Chemistry. 2020;2020(3):295-305
Jovanović, M., Petković, M., Jovanović, P., Simić, M., Tasić, G., Erić, S.,& Savić, V. (2020). Proline Derived Bicyclic Derivatives through Metal Catalysed Cyclisations of Allenes: Synthesis of Longamide B, Stylisine D and their Derivatives.
European Journal of Organic ChemistryWiley-Blackwell., 2020(3), 295-305.
https://doi.org/10.1002/ejoc.201901554
Jovanović Miloš, Petković Miloš, Jovanović Predrag, Simić Milena, Tasić Gordana, Erić Slavica, Savić Vladimir, "Proline Derived Bicyclic Derivatives through Metal Catalysed Cyclisations of Allenes: Synthesis of Longamide B, Stylisine D and their Derivatives" 2020, no. 3 (2020):295-305,
https://doi.org/10.1002/ejoc.201901554 .
