Asymmetric Total Synthesis of Leptosphin C

A concise enantioselective total synthesis of leptosphine C (<b>1</b>) has been achieved. Our synthetic strategy features an unprecedented diastereo-/enantioselective Hajos-Parrish-Eder-Sauer-Wiechert (HPESW) reaction for construction of the AB ring system with continuous stereogenic centers (76% yield, 90% ee, dr = 19:1) and an uncommon Pauson-Khand (PK) reaction of geminal dimethyl alkenyl side chains for establishing the CD ring system with the quaternary carbon at C14.

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Publication Details

Journal
Organic Letters
Published
2025-08-26
DOI
https://doi.org/10.1021/acs.orglett.5c03236
Primary Topic
Chemical synthesis and alkaloids
Type
article
Field-Weighted Citation Impact
0.00

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article

Asymmetric Total Synthesis of Leptosphin C

Lantian Sun, Chenshan Lian, Chi‐Sing Lee, Zigang Li et al.
Organic Letters
Chemical synthesis and alkaloids
article

Asymmetric Total Synthesis of Leptosphin C

Lantian Sun, Chenshan Lian, Chi‐Sing Lee, Zigang Li, Xiaole Chen, Jingyi Zhao, Wei Han
article en

Abstract

A concise enantioselective total synthesis of leptosphine C (<b>1</b>) has been achieved. Our synthetic strategy features an unprecedented diastereo-/enantioselective Hajos-Parrish-Eder-Sauer-Wiechert (HPESW) reaction for construction of the AB ring system with continuous stereogenic centers (76% yield, 90% ee, dr = 19:1) and an uncommon Pauson-Khand (PK) reaction of geminal dimethyl alkenyl side chains for establishing the CD ring system with the quaternary carbon at C14.

Organic LettersVol. 27(35)
Hong Kong Baptist University (HK), University Town of Shenzhen (CN)
Hong Kong Baptist University, National Natural Science Foundation of China, Research Grants Council, University Grants Committee, Peking University, Shenzhen Graduate School, Peking University
Zero hunger
Openalex Percentile: Top 83%
Chemical synthesis and alkaloids
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Asymmetric Total Synthesis of Leptosphin C — Lantian Sun, Chenshan Lian, et al. · Organic Letters (2025) | TGRS Research Map | TGRS