Proline Derived Bicyclic Derivatives through Metal Catalysed Cyclisations of Allenes: Synthesis of Longamide B, Stylisine D and their Derivatives
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2020
Authors
Jovanović, MilošPetković, Miloš
Jovanović, Predrag
Simić, Milena
Tasić, Gordana
Erić, Slavica
Savić, Vladimir
Article (Published version)
Metadata
Show full item recordAbstract
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 DSource:
European Journal of Organic Chemistry, 2020, 2020, 3, 295-305Publisher:
- Wiley-Blackwell
Funding / projects:
- Computational design, synthesis and biological evaluation of new heterocyclic compounds as selective tumorogenesis inhibitors (RS-MESTD-Basic Research (BR or ON)-172009)
DOI: 10.1002/ejoc.201901554
ISSN: 1434-193X
WoS: 000501722100001
Scopus: 2-s2.0-85076378351
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PharmacyTY - 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 - https://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", 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.. (2020). Proline Derived Bicyclic Derivatives through Metal Catalysed Cyclisations of Allenes: Synthesis of Longamide B, Stylisine D and their Derivatives. in European Journal of Organic Chemistry Wiley-Blackwell., 2020(3), 295-305. https://doi.org/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. in European Journal of Organic Chemistry. 2020;2020(3):295-305. doi: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" in European Journal of Organic Chemistry, 2020, no. 3 (2020):295-305, https://doi.org/10.1002/ejoc.201901554 . .