Asymmetric Total Syntheses of Kopsane Alkaloids via a PtCl2-Catalyzed Intramolecular [3+2] Cycloaddition

Xuelei Jia; Honghui Lei; Feipeng Han; Tao Zhang; Ying Chen; Zhengshuang Xu; Pratanphorn Nakliang; Sun Choi; Yian Guo; Tao Ye

doi:10.1002/anie.202005048

Asymmetric Total Syntheses of Kopsane Alkaloids via a PtCl₂-Catalyzed Intramolecular [3+2] Cycloaddition

Xuelei Jia, Honghui Lei, Feipeng Han, Tao Zhang, Ying Chen, Zhengshuang Xu, Pratanphorn Nakliang, Sun Choi, Yian Guo, Tao Ye

Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

Abstract

A concise and asymmetric total synthesis of five kopsane alkaloids that share a unique heptacyclic caged ring system was accomplished. The key transformation in the sequence involved a remarkable PtCl₂-catalyzed intramolecular [3+2] cycloaddition, which allowed for the rapid assembly of pentacyclic carbon skeletons bearing 2,3-quaternary functionalized indoline. Expeditious construction of diverse indoline scaffolds with excellent control of diastereoselectivity demonstrated the broad scope and versatility of this key transformation.

Original language	English
Pages (from-to)	12832-12836
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	59
Issue number	31
DOIs	https://doi.org/10.1002/anie.202005048
State	Published - 27 Jul 2020

Bibliographical note

Funding Information:
We acknowledge financial support from the National Natural Science Foundation of China (21772009, 21901013), the Shenzhen Peacock Plan (KQTD2015071714043444), the Shenzhen Science and Technology Innovation Commission (JCYJ20170818090017617, JCYJ20170818090238288), the GDNSF (2014B030301003), the National Research Foundation of Korea (NRF) grants funded by the Ministry of Science and ICT (MSIT; NRF-2017R1A2B4010084, 2018R1A5A2025286, NRF-2019M3E5D4065251), and a Peng Cheng Scholar (to S.C.). Moreover, we thank the Korea Institute of Science and Technology Information (KISTI) Supercomputing Center for providing computing resources. This work was also inspired by the international and interdisciplinary environments of the JSPS Asian CORE Program, “Asian Chemical Biology Initiative”.

Funding Information:
We acknowledge financial support from the National Natural Science Foundation of China (21772009, 21901013), the Shenzhen Peacock Plan (KQTD2015071714043444), the Shenzhen Science and Technology Innovation Commission (JCYJ20170818090017617, JCYJ20170818090238288), the GDNSF (2014B030301003), the National Research Foundation of Korea (NRF) grants funded by the Ministry of Science and ICT (MSIT; NRF‐2017R1A2B4010084, 2018R1A5A2025286, NRF‐2019M3E5D4065251), and a Peng Cheng Scholar (to S.C.). Moreover, we thank the Korea Institute of Science and Technology Information (KISTI) Supercomputing Center for providing computing resources. This work was also inspired by the international and interdisciplinary environments of the JSPS Asian CORE Program, “Asian Chemical Biology Initiative”.

Publisher Copyright:
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

Pt catalysis
[3+2] cycloaddition reactions
alkaloids
kopsanes
natural products

Access to Document

10.1002/anie.202005048

Cite this

@article{8747c0a0f4ab404c913e85eecfae2f4e,

title = "Asymmetric Total Syntheses of Kopsane Alkaloids via a PtCl2-Catalyzed Intramolecular [3+2] Cycloaddition",

abstract = "A concise and asymmetric total synthesis of five kopsane alkaloids that share a unique heptacyclic caged ring system was accomplished. The key transformation in the sequence involved a remarkable PtCl2-catalyzed intramolecular [3+2] cycloaddition, which allowed for the rapid assembly of pentacyclic carbon skeletons bearing 2,3-quaternary functionalized indoline. Expeditious construction of diverse indoline scaffolds with excellent control of diastereoselectivity demonstrated the broad scope and versatility of this key transformation.",

keywords = "Pt catalysis, [3+2] cycloaddition reactions, alkaloids, kopsanes, natural products",

author = "Xuelei Jia and Honghui Lei and Feipeng Han and Tao Zhang and Ying Chen and Zhengshuang Xu and Pratanphorn Nakliang and Sun Choi and Yian Guo and Tao Ye",

note = "Funding Information: We acknowledge financial support from the National Natural Science Foundation of China (21772009, 21901013), the Shenzhen Peacock Plan (KQTD2015071714043444), the Shenzhen Science and Technology Innovation Commission (JCYJ20170818090017617, JCYJ20170818090238288), the GDNSF (2014B030301003), the National Research Foundation of Korea (NRF) grants funded by the Ministry of Science and ICT (MSIT; NRF-2017R1A2B4010084, 2018R1A5A2025286, NRF-2019M3E5D4065251), and a Peng Cheng Scholar (to S.C.). Moreover, we thank the Korea Institute of Science and Technology Information (KISTI) Supercomputing Center for providing computing resources. This work was also inspired by the international and interdisciplinary environments of the JSPS Asian CORE Program, “Asian Chemical Biology Initiative”. Funding Information: We acknowledge financial support from the National Natural Science Foundation of China (21772009, 21901013), the Shenzhen Peacock Plan (KQTD2015071714043444), the Shenzhen Science and Technology Innovation Commission (JCYJ20170818090017617, JCYJ20170818090238288), the GDNSF (2014B030301003), the National Research Foundation of Korea (NRF) grants funded by the Ministry of Science and ICT (MSIT; NRF‐2017R1A2B4010084, 2018R1A5A2025286, NRF‐2019M3E5D4065251), and a Peng Cheng Scholar (to S.C.). Moreover, we thank the Korea Institute of Science and Technology Information (KISTI) Supercomputing Center for providing computing resources. This work was also inspired by the international and interdisciplinary environments of the JSPS Asian CORE Program, “Asian Chemical Biology Initiative”. Publisher Copyright: {\textcopyright} 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2020",

month = jul,

day = "27",

doi = "10.1002/anie.202005048",

language = "English",

volume = "59",

pages = "12832--12836",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "31",

}

TY - JOUR

T1 - Asymmetric Total Syntheses of Kopsane Alkaloids via a PtCl2-Catalyzed Intramolecular [3+2] Cycloaddition

AU - Jia, Xuelei

AU - Lei, Honghui

AU - Han, Feipeng

AU - Zhang, Tao

AU - Chen, Ying

AU - Xu, Zhengshuang

AU - Nakliang, Pratanphorn

AU - Choi, Sun

AU - Guo, Yian

AU - Ye, Tao

N1 - Funding Information: We acknowledge financial support from the National Natural Science Foundation of China (21772009, 21901013), the Shenzhen Peacock Plan (KQTD2015071714043444), the Shenzhen Science and Technology Innovation Commission (JCYJ20170818090017617, JCYJ20170818090238288), the GDNSF (2014B030301003), the National Research Foundation of Korea (NRF) grants funded by the Ministry of Science and ICT (MSIT; NRF-2017R1A2B4010084, 2018R1A5A2025286, NRF-2019M3E5D4065251), and a Peng Cheng Scholar (to S.C.). Moreover, we thank the Korea Institute of Science and Technology Information (KISTI) Supercomputing Center for providing computing resources. This work was also inspired by the international and interdisciplinary environments of the JSPS Asian CORE Program, “Asian Chemical Biology Initiative”. Funding Information: We acknowledge financial support from the National Natural Science Foundation of China (21772009, 21901013), the Shenzhen Peacock Plan (KQTD2015071714043444), the Shenzhen Science and Technology Innovation Commission (JCYJ20170818090017617, JCYJ20170818090238288), the GDNSF (2014B030301003), the National Research Foundation of Korea (NRF) grants funded by the Ministry of Science and ICT (MSIT; NRF‐2017R1A2B4010084, 2018R1A5A2025286, NRF‐2019M3E5D4065251), and a Peng Cheng Scholar (to S.C.). Moreover, we thank the Korea Institute of Science and Technology Information (KISTI) Supercomputing Center for providing computing resources. This work was also inspired by the international and interdisciplinary environments of the JSPS Asian CORE Program, “Asian Chemical Biology Initiative”. Publisher Copyright: © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2020/7/27

Y1 - 2020/7/27

N2 - A concise and asymmetric total synthesis of five kopsane alkaloids that share a unique heptacyclic caged ring system was accomplished. The key transformation in the sequence involved a remarkable PtCl2-catalyzed intramolecular [3+2] cycloaddition, which allowed for the rapid assembly of pentacyclic carbon skeletons bearing 2,3-quaternary functionalized indoline. Expeditious construction of diverse indoline scaffolds with excellent control of diastereoselectivity demonstrated the broad scope and versatility of this key transformation.

AB - A concise and asymmetric total synthesis of five kopsane alkaloids that share a unique heptacyclic caged ring system was accomplished. The key transformation in the sequence involved a remarkable PtCl2-catalyzed intramolecular [3+2] cycloaddition, which allowed for the rapid assembly of pentacyclic carbon skeletons bearing 2,3-quaternary functionalized indoline. Expeditious construction of diverse indoline scaffolds with excellent control of diastereoselectivity demonstrated the broad scope and versatility of this key transformation.

KW - Pt catalysis

KW - [3+2] cycloaddition reactions

KW - alkaloids

KW - kopsanes

KW - natural products

UR - http://www.scopus.com/inward/record.url?scp=85085543262&partnerID=8YFLogxK

U2 - 10.1002/anie.202005048

DO - 10.1002/anie.202005048

M3 - Article

C2 - 32329945

AN - SCOPUS:85085543262

SN - 1433-7851

VL - 59

SP - 12832

EP - 12836

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 31

ER -