Synthesis of the Tricyclic Picrotoxane Motif by an Oxidative Cascade Cyclization

Jingming Cao; Waygen Thor; Shenkun Yang; Mengxun Zhang; Wenli Bao; Lizhi Zhu; Wei Yang; Yuen Kit Cheng; Chi Sing Lee

doi:10.1021/acs.orglett.9b01806

Synthesis of the Tricyclic Picrotoxane Motif by an Oxidative Cascade Cyclization

Jingming Cao
, Waygen Thor
, Shenkun Yang
, Mengxun Zhang
, Wenli Bao
, Lizhi Zhu
, Wei Yang^*
, Yuen Kit Cheng
, Chi Sing Lee

^*Corresponding author for this work

Department of Chemistry

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

21 Citations (Scopus)

Abstract

An oxidative cascade cyclization of β-keto esters has been developed for the construction of the tricyclic picrotoxane motif in a single step, and DFT calculations suggested a possible cationic cyclization mechanism. This cascade cyclization can be operated on a 20 g scale to obtain a 77% total yield of the tricyclic products, which in turn can be converted to versatile intermediates for further elaboration to picrotoxanes and their structurally related compounds.

Original language	English
Pages (from-to)	4896-4899
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	12
DOIs	https://doi.org/10.1021/acs.orglett.9b01806
Publication status	Published - 21 Jun 2019

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10.1021/acs.orglett.9b01806

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@article{401e363898334e52bfa8cbbdca0e36fc,

title = "Synthesis of the Tricyclic Picrotoxane Motif by an Oxidative Cascade Cyclization",

abstract = "An oxidative cascade cyclization of β-keto esters has been developed for the construction of the tricyclic picrotoxane motif in a single step, and DFT calculations suggested a possible cationic cyclization mechanism. This cascade cyclization can be operated on a 20 g scale to obtain a 77\% total yield of the tricyclic products, which in turn can be converted to versatile intermediates for further elaboration to picrotoxanes and their structurally related compounds.",

author = "Jingming Cao and Waygen Thor and Shenkun Yang and Mengxun Zhang and Wenli Bao and Lizhi Zhu and Wei Yang and Cheng, \{Yuen Kit\} and Lee, \{Chi Sing\}",

note = "Funding Information: We gratefully acknowledge the National Natural Science Foundation of China (Grants 21502002, 21572006, and 21871017), the Natural Science Foundation of Guangdong Province, China (Grant 2017A030313042), the Shenzhen Science and Technology Innovation Committee (Grants JCYJ20160428153421635 and JCYJ20160330095659560), and Peking University Shenzhen Graduate School and Hong Kong Baptist University (RC-SGT2/18-19/SCI/005) for financial support. A special acknowledgement is made to Dr. Wesley Ting-kwok Chan (Hong Kong Polytechnic University) for the X-ray crystallography characterization of compounds (±)-15. Publisher copyright: {\textcopyright} 2019 American Chemical Society",

year = "2019",

month = jun,

day = "21",

doi = "10.1021/acs.orglett.9b01806",

language = "English",

volume = "21",

pages = "4896--4899",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "12",

}

TY - JOUR

T1 - Synthesis of the Tricyclic Picrotoxane Motif by an Oxidative Cascade Cyclization

AU - Cao, Jingming

AU - Thor, Waygen

AU - Yang, Shenkun

AU - Zhang, Mengxun

AU - Bao, Wenli

AU - Zhu, Lizhi

AU - Yang, Wei

AU - Cheng, Yuen Kit

AU - Lee, Chi Sing

N1 - Funding Information: We gratefully acknowledge the National Natural Science Foundation of China (Grants 21502002, 21572006, and 21871017), the Natural Science Foundation of Guangdong Province, China (Grant 2017A030313042), the Shenzhen Science and Technology Innovation Committee (Grants JCYJ20160428153421635 and JCYJ20160330095659560), and Peking University Shenzhen Graduate School and Hong Kong Baptist University (RC-SGT2/18-19/SCI/005) for financial support. A special acknowledgement is made to Dr. Wesley Ting-kwok Chan (Hong Kong Polytechnic University) for the X-ray crystallography characterization of compounds (±)-15. Publisher copyright: © 2019 American Chemical Society

PY - 2019/6/21

Y1 - 2019/6/21

N2 - An oxidative cascade cyclization of β-keto esters has been developed for the construction of the tricyclic picrotoxane motif in a single step, and DFT calculations suggested a possible cationic cyclization mechanism. This cascade cyclization can be operated on a 20 g scale to obtain a 77% total yield of the tricyclic products, which in turn can be converted to versatile intermediates for further elaboration to picrotoxanes and their structurally related compounds.

AB - An oxidative cascade cyclization of β-keto esters has been developed for the construction of the tricyclic picrotoxane motif in a single step, and DFT calculations suggested a possible cationic cyclization mechanism. This cascade cyclization can be operated on a 20 g scale to obtain a 77% total yield of the tricyclic products, which in turn can be converted to versatile intermediates for further elaboration to picrotoxanes and their structurally related compounds.

UR - https://www.scopus.com/pages/publications/85067655277

U2 - 10.1021/acs.orglett.9b01806

DO - 10.1021/acs.orglett.9b01806

M3 - Journal article

C2 - 31188619

AN - SCOPUS:85067655277

SN - 1523-7060

VL - 21

SP - 4896

EP - 4899

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Synthesis of the Tricyclic Picrotoxane Motif by an Oxidative Cascade Cyclization

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