Asymmetric Total Synthesis of Leptosphin C

Lantian Sun; Chenshan Lian; Jingyi Zhao; Xiaole Chen; Wei Han; Zigang Li; Chi-Sing Lee

doi:10.1021/acs.orglett.5c03236

Asymmetric Total Synthesis of Leptosphin C

Lantian Sun
, Chenshan Lian
, Jingyi Zhao
, Xiaole Chen
, Wei Han^*
, Zigang Li^*
, Chi-Sing Lee^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

Abstract

A concise enantioselective total synthesis of leptosphine C (1) 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.

Original language	English
Pages (from-to)	9814-9819
Number of pages	6
Journal	Organic Letters
Volume	27
Issue number	35
Early online date	26 Aug 2025
DOIs	https://doi.org/10.1021/acs.orglett.5c03236
Publication status	Published - 5 Sept 2025

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 9 Industry, Innovation, and Infrastructure

Access to Document

10.1021/acs.orglett.5c03236

Cite this

@article{3577757ee1d847f9bbf2227d2d82775e,

title = "Asymmetric Total Synthesis of Leptosphin C",

abstract = "A concise enantioselective total synthesis of leptosphine C (1) 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.",

author = "Lantian Sun and Chenshan Lian and Jingyi Zhao and Xiaole Chen and Wei Han and Zigang Li and Chi-Sing Lee",

note = "This work is financially supported by the National Natural Science Foundation of China (grant no. 22471231), Research Grants Council of Hong Kong (HKBU 12301320 and 12303821), Hong Kong Baptist University, and Peking University Shenzhen Graduate School. Publisher copyright: {\textcopyright} 2025 The Authors. Published by American Chemical Society.",

year = "2025",

month = sep,

day = "5",

doi = "10.1021/acs.orglett.5c03236",

language = "English",

volume = "27",

pages = "9814--9819",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "35",

}

TY - JOUR

T1 - Asymmetric Total Synthesis of Leptosphin C

AU - Sun, Lantian

AU - Lian, Chenshan

AU - Zhao, Jingyi

AU - Chen, Xiaole

AU - Han, Wei

AU - Li, Zigang

AU - Lee, Chi-Sing

N1 - This work is financially supported by the National Natural Science Foundation of China (grant no. 22471231), Research Grants Council of Hong Kong (HKBU 12301320 and 12303821), Hong Kong Baptist University, and Peking University Shenzhen Graduate School. Publisher copyright: © 2025 The Authors. Published by American Chemical Society.

PY - 2025/9/5

Y1 - 2025/9/5

N2 - A concise enantioselective total synthesis of leptosphine C (1) 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.

AB - A concise enantioselective total synthesis of leptosphine C (1) 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.

UR - https://www.scopus.com/pages/publications/105015577172

U2 - 10.1021/acs.orglett.5c03236

DO - 10.1021/acs.orglett.5c03236

M3 - Journal article

C2 - 40857143

SN - 1523-7060

VL - 27

SP - 9814

EP - 9819

JO - Organic Letters

JF - Organic Letters

IS - 35

ER -

Asymmetric Total Synthesis of Leptosphin C

Abstract

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this