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Recent total synthesis of natural products leveraging a strategy of enamide cyclization

Chun-Yu Mi, Jia-Yuan Zhai and Xiao-Ming Zhang

Beilstein J. Org. Chem. 2025, 21, 999–1009. https://doi.org/10.3762/bjoc.21.81

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Chun-Yu Mi, Jia-Yuan Zhai and Xiao-Ming Zhang

Beilstein J. Org. Chem. 2025, 21, 999–1009. https://doi.org/10.3762/bjoc.21.81

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Mi, C.-Y.; Zhai, J.-Y.; Zhang, X.-M. Beilstein J. Org. Chem. 2025, 21, 999–1009. doi:10.3762/bjoc.21.81

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TY  - JOUR
A1  - Mi, Chun-Yu
A1  - Zhai, Jia-Yuan
A1  - Zhang, Xiao-Ming
T1  - Recent total synthesis of natural products leveraging a strategy of enamide cyclization
JF  - Beilstein Journal of Organic Chemistry
PY  - 2025///
VL  - 21
SP  - 999
EP  - 1009
SN  - 1860-5397
DO  - 10.3762/bjoc.21.81
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.21.81
KW  - alkaloid
KW  - cyclization
KW  - enamide
KW  - natural product
KW  - total synthesis
N2  - Enamides are distinctive amphiphilic synthons that can be strategically incorporated into cyclization reactions. The iminium species generated from enamides via nucleophilic addition or substitution are capable of engaging in further electrophilic additions or isomerization processes. Exploiting the multiple reactivities of enamides facilitates the development of diverse cyclization modes that provide entries to various N-heterocycles, some of which serve as key structural motifs in natural alkaloids. This review highlights recent advancements in enamide-based cyclization reactions, including enamide–alkyne cycloisomerization, [3 + 2] annulation, and polycyclization, with a particular emphasis on their pivotal role as a strategy in the total synthesis of natural products.
ER  -

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aromatic	the word “aromatic”
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