Short Formal Syntheses of Lycorine and Congeners Using a 5-Endo-Trig/6-Endo-Trig Radical Cyclization Sequence

Shen Tan; Samir Z. Zard; Le Nhan Pham; Michelle L. Coote; Martin G. Banwell; Ping Lan; Lorenzo V. White

doi:10.1021/acs.orglett.4c01271

Short Formal Syntheses of Lycorine and Congeners Using a 5-Endo-Trig/6-Endo-Trig Radical Cyclization Sequence

Shen Tan, Samir Z. Zard, Le Nhan Pham, Michelle L. Coote, Martin G. Banwell, Ping Lan, Lorenzo V. White

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Abstract

Here, we report a practical route to medicinally interesting lycorine congeners alongside formal syntheses of various lycorine-type natural products, including lycorine itself. The efficiency of our strategy derives from a back-to-back 5-endo-trig/6-endo-trig radical cyclization sequence, which we systematically studied both experimentally and computationally. The results of our work will facilitate future development of urgently needed antiviral therapeutics based on lycorine.

Original language	English
Pages (from-to)	4292-4296
Number of pages	5
Journal	Organic Letters
Volume	26
Issue number	20
Early online date	10 May 2024
DOIs	https://doi.org/10.1021/acs.orglett.4c01271
Publication status	Published - 24 May 2024

Keywords

Anions
Cyclization
Mixtures
Molecular structure
Organic reactions

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10.1021/acs.orglett.4c01271Licence: In Copyright

Accepted author manuscriptAccepted author manuscript, 1.18 MBLicence: In Copyright

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abstract = "Here, we report a practical route to medicinally interesting lycorine congeners alongside formal syntheses of various lycorine-type natural products, including lycorine itself. The efficiency of our strategy derives from a back-to-back 5-endo-trig/6-endo-trig radical cyclization sequence, which we systematically studied both experimentally and computationally. The results of our work will facilitate future development of urgently needed antiviral therapeutics based on lycorine.",

keywords = "Anions, Cyclization, Mixtures, Molecular structure, Organic reactions",

author = "Shen Tan and Zard, {Samir Z.} and Pham, {Le Nhan} and Coote, {Michelle L.} and Banwell, {Martin G.} and Ping Lan and White, {Lorenzo V.}",

year = "2024",

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T1 - Short Formal Syntheses of Lycorine and Congeners Using a 5-Endo-Trig/6-Endo-Trig Radical Cyclization Sequence

AU - Tan, Shen

AU - Zard, Samir Z.

AU - Pham, Le Nhan

AU - Coote, Michelle L.

AU - Banwell, Martin G.

AU - Lan, Ping

AU - White, Lorenzo V.

PY - 2024/5/24

Y1 - 2024/5/24

N2 - Here, we report a practical route to medicinally interesting lycorine congeners alongside formal syntheses of various lycorine-type natural products, including lycorine itself. The efficiency of our strategy derives from a back-to-back 5-endo-trig/6-endo-trig radical cyclization sequence, which we systematically studied both experimentally and computationally. The results of our work will facilitate future development of urgently needed antiviral therapeutics based on lycorine.

AB - Here, we report a practical route to medicinally interesting lycorine congeners alongside formal syntheses of various lycorine-type natural products, including lycorine itself. The efficiency of our strategy derives from a back-to-back 5-endo-trig/6-endo-trig radical cyclization sequence, which we systematically studied both experimentally and computationally. The results of our work will facilitate future development of urgently needed antiviral therapeutics based on lycorine.

KW - Anions

KW - Cyclization

KW - Mixtures

KW - Molecular structure

KW - Organic reactions

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UR - http://purl.org/au-research/grants/ARC/DP210100025

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SP - 4292

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JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

Short Formal Syntheses of Lycorine and Congeners Using a 5-Endo-Trig/6-Endo-Trig Radical Cyclization Sequence

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