Recent Advances in Construction of Polycyclic Natural Product Scaffolds via One-Pot Reactions Involving Alkyne Annulation
Polycyclic scaffolds are omnipresent in natural products and drugs, and the synthetic strategies and methods toward construction of these scaffolds are of particular importance. Compared to simple cyclic ring systems, polycyclic scaffolds have higher structure complexity and diversity, making them s...
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2020-10-01
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doaj-db0441b070c84eb0913266a18b70feee2020-11-25T03:55:00ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462020-10-01810.3389/fchem.2020.580355580355Recent Advances in Construction of Polycyclic Natural Product Scaffolds via One-Pot Reactions Involving Alkyne AnnulationLiyao Zheng0Ruimao Hua1School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou, ChinaDepartment of Chemistry, Tsinghua University, Beijing, ChinaPolycyclic scaffolds are omnipresent in natural products and drugs, and the synthetic strategies and methods toward construction of these scaffolds are of particular importance. Compared to simple cyclic ring systems, polycyclic scaffolds have higher structure complexity and diversity, making them suitable for charting broader chemical space, yet bringing challenges for the syntheses. In this review, we surveyed progress in the past decade on synthetic methods for polycyclic natural product scaffolds, in which the key steps are one-pot reactions involving intermolecular or intramolecular alkyne annulation. Synthetic strategies of selected polycyclic carbocycles and heterocycles with at least three fused, bridged, or spiro rings are discussed with emphasis on the synthetic efficiency and product diversity. Recent examples containing newly developed synthetic concepts or toolkits such as collective and divergent total synthesis, gold catalysis, C–H functionalization, and dearomative cyclization are highlighted. Finally, several “privileged synthetic strategies” for “privileged polycyclic scaffolds” are summarized, with discussion of remained challenges and future perspectives.https://www.frontiersin.org/article/10.3389/fchem.2020.580355/fullone-pot reactioncascade cyclizationalkynescarbocyclesheterocyclesnatural products |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Liyao Zheng Ruimao Hua |
spellingShingle |
Liyao Zheng Ruimao Hua Recent Advances in Construction of Polycyclic Natural Product Scaffolds via One-Pot Reactions Involving Alkyne Annulation Frontiers in Chemistry one-pot reaction cascade cyclization alkynes carbocycles heterocycles natural products |
author_facet |
Liyao Zheng Ruimao Hua |
author_sort |
Liyao Zheng |
title |
Recent Advances in Construction of Polycyclic Natural Product Scaffolds via One-Pot Reactions Involving Alkyne Annulation |
title_short |
Recent Advances in Construction of Polycyclic Natural Product Scaffolds via One-Pot Reactions Involving Alkyne Annulation |
title_full |
Recent Advances in Construction of Polycyclic Natural Product Scaffolds via One-Pot Reactions Involving Alkyne Annulation |
title_fullStr |
Recent Advances in Construction of Polycyclic Natural Product Scaffolds via One-Pot Reactions Involving Alkyne Annulation |
title_full_unstemmed |
Recent Advances in Construction of Polycyclic Natural Product Scaffolds via One-Pot Reactions Involving Alkyne Annulation |
title_sort |
recent advances in construction of polycyclic natural product scaffolds via one-pot reactions involving alkyne annulation |
publisher |
Frontiers Media S.A. |
series |
Frontiers in Chemistry |
issn |
2296-2646 |
publishDate |
2020-10-01 |
description |
Polycyclic scaffolds are omnipresent in natural products and drugs, and the synthetic strategies and methods toward construction of these scaffolds are of particular importance. Compared to simple cyclic ring systems, polycyclic scaffolds have higher structure complexity and diversity, making them suitable for charting broader chemical space, yet bringing challenges for the syntheses. In this review, we surveyed progress in the past decade on synthetic methods for polycyclic natural product scaffolds, in which the key steps are one-pot reactions involving intermolecular or intramolecular alkyne annulation. Synthetic strategies of selected polycyclic carbocycles and heterocycles with at least three fused, bridged, or spiro rings are discussed with emphasis on the synthetic efficiency and product diversity. Recent examples containing newly developed synthetic concepts or toolkits such as collective and divergent total synthesis, gold catalysis, C–H functionalization, and dearomative cyclization are highlighted. Finally, several “privileged synthetic strategies” for “privileged polycyclic scaffolds” are summarized, with discussion of remained challenges and future perspectives. |
topic |
one-pot reaction cascade cyclization alkynes carbocycles heterocycles natural products |
url |
https://www.frontiersin.org/article/10.3389/fchem.2020.580355/full |
work_keys_str_mv |
AT liyaozheng recentadvancesinconstructionofpolycyclicnaturalproductscaffoldsviaonepotreactionsinvolvingalkyneannulation AT ruimaohua recentadvancesinconstructionofpolycyclicnaturalproductscaffoldsviaonepotreactionsinvolvingalkyneannulation |
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