Asymmetric Total Synthesis of Neobraclactone C

Xinhang Zhang; Hanyang Sun; Changhong Han; He Wang; Junpeng Zhang; Di Zhang; Bin Lin; Huiming Hua; Maosheng Cheng; Yongxiang Liu

doi:10.1021/acs.orglett.2c03970

Asymmetric Total Synthesis of Neobraclactone C

Org Lett. 2022 Dec 30;24(51):9485-9490. doi: 10.1021/acs.orglett.2c03970. Epub 2022 Dec 15.

Authors

Xinhang Zhang^{1

2

3}, Hanyang Sun^{1

2

3}, Changhong Han^{1

2

3}, He Wang^{1

2

3}, Junpeng Zhang^{1

3}, Di Zhang^{1

3}, Bin Lin^{1

2

3}, Huiming Hua¹, Maosheng Cheng^{1

3}, Yongxiang Liu^{1

2

3}

Affiliations

¹ Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, People's Republic of China.
² Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, People's Republic of China.
³ Institute of Drug Research in Medicine Capital of China, Benxi, Liaoning 117000, People's Republic of China.

PMID: 36520595
DOI: 10.1021/acs.orglett.2c03970

Abstract

Asymmetric total synthesis of neobraclactone C was finished for the first time using the convergent synthetic strategy in 22 steps in the longest linear sequence from known materials. The key steps include a steric hindrance/hydrogen bond dual-controlled Heck arylation of α,β-unsaturated ketone to construct hemiketal and cis-alkenyl in one step and a CeCl₃-catalyzed tricycle formation.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Molecular Structure
Palladium* / chemistry
Stereoisomerism

Substances

Palladium