Total Synthesis of (+)-Norsecurinamine B

Norsecurinamine B represents the first example of an NH-bridged dimeric <i>Securinega</i> alkaloid, in which two norsecurinine monomers are joined through an amine linker at their <i>endo</i> faces. However, the <i>exo</i> face of norsecurinine is intrinsically favored for nucleophilic attack, rendering the synthesis of the target challenging. Herein, we disclose a convergent total synthesis of norsecurinamine B, highlighting the strategic design elements that effectively address this stereochemical challenge.

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Publication Details

Journal
Organic Letters
Published
2025-12-05
DOI
https://doi.org/10.1021/acs.orglett.5c04792
Primary Topic
Phytochemistry and Bioactivity Studies
Type
article
Field-Weighted Citation Impact
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article

Total Synthesis of (+)-Norsecurinamine B

Sugyeong Seo, Sunkyu Han, M. SHIN
Organic Letters
Phytochemistry and Bioactivity Studies
article

Total Synthesis of (+)-Norsecurinamine B

Sugyeong Seo, Sunkyu Han, M. SHIN
article en

Abstract

Norsecurinamine B represents the first example of an NH-bridged dimeric <i>Securinega</i> alkaloid, in which two norsecurinine monomers are joined through an amine linker at their <i>endo</i> faces. However, the <i>exo</i> face of norsecurinine is intrinsically favored for nucleophilic attack, rendering the synthesis of the target challenging. Herein, we disclose a convergent total synthesis of norsecurinamine B, highlighting the strategic design elements that effectively address this stereochemical challenge.

Organic LettersVol. 27(50)
Korea Advanced Institute of Science and Technology (KR)
Openalex Percentile: Top 53%
Phytochemistry and Bioactivity Studies
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