Exploration of 1,3-dipolar cycloaddition reactions to construct the core skeleton of Calyciphylline A-type alkaloids

Jiaxin Zhong; Haibing He; Shuanhu Gao

doi:10.1039/c9qo01111k

Exploration of 1,3-dipolar cycloaddition reactions to construct the core skeleton of Calyciphylline A-type alkaloids

Jiaxin Zhong
, Haibing He^*
, Shuanhu Gao

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

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

14 Scopus citations

Abstract

Nitrone induced 1,3-dipolar [3 + 2] cycloadditions were studied to construct the core structure of Calyciphylline A-type Daphniphyllum alkaloids. This approach is capable of installing the cis-hydroindole A-C ring as well as the spiro-A-C-E ring with the all-carbon quaternary centers at C-5 and C-8, and has been successfully used in the total synthesis of himalensine A. It also lays the foundation for the synthesis of challenging Calyciphylline A-type alkaloids, such as daphniyunnine A.

Original language	English
Pages (from-to)	3781-3785
Number of pages	5
Journal	Organic Chemistry Frontiers
Volume	6
Issue number	22
DOIs	https://doi.org/10.1039/c9qo01111k
State	Published - 21 Nov 2019

Access to Document

10.1039/c9qo01111k

Cite this

@article{22f27700fab340ba80d612ced2a83c62,

title = "Exploration of 1,3-dipolar cycloaddition reactions to construct the core skeleton of Calyciphylline A-type alkaloids",

abstract = "Nitrone induced 1,3-dipolar [3 + 2] cycloadditions were studied to construct the core structure of Calyciphylline A-type Daphniphyllum alkaloids. This approach is capable of installing the cis-hydroindole A-C ring as well as the spiro-A-C-E ring with the all-carbon quaternary centers at C-5 and C-8, and has been successfully used in the total synthesis of himalensine A. It also lays the foundation for the synthesis of challenging Calyciphylline A-type alkaloids, such as daphniyunnine A.",

author = "Jiaxin Zhong and Haibing He and Shuanhu Gao",

note = "Publisher Copyright: {\textcopyright} 2019 the Partner Organisations.",

year = "2019",

month = nov,

day = "21",

doi = "10.1039/c9qo01111k",

language = "英语",

volume = "6",

pages = "3781--3785",

journal = "Organic Chemistry Frontiers",

issn = "2052-4110",

publisher = "Royal Society of Chemistry",

number = "22",

}

TY - JOUR

T1 - Exploration of 1,3-dipolar cycloaddition reactions to construct the core skeleton of Calyciphylline A-type alkaloids

AU - Zhong, Jiaxin

AU - He, Haibing

AU - Gao, Shuanhu

PY - 2019/11/21

Y1 - 2019/11/21

N2 - Nitrone induced 1,3-dipolar [3 + 2] cycloadditions were studied to construct the core structure of Calyciphylline A-type Daphniphyllum alkaloids. This approach is capable of installing the cis-hydroindole A-C ring as well as the spiro-A-C-E ring with the all-carbon quaternary centers at C-5 and C-8, and has been successfully used in the total synthesis of himalensine A. It also lays the foundation for the synthesis of challenging Calyciphylline A-type alkaloids, such as daphniyunnine A.

AB - Nitrone induced 1,3-dipolar [3 + 2] cycloadditions were studied to construct the core structure of Calyciphylline A-type Daphniphyllum alkaloids. This approach is capable of installing the cis-hydroindole A-C ring as well as the spiro-A-C-E ring with the all-carbon quaternary centers at C-5 and C-8, and has been successfully used in the total synthesis of himalensine A. It also lays the foundation for the synthesis of challenging Calyciphylline A-type alkaloids, such as daphniyunnine A.

UR - https://www.scopus.com/pages/publications/85074656510

U2 - 10.1039/c9qo01111k

DO - 10.1039/c9qo01111k

M3 - 文章

AN - SCOPUS:85074656510

SN - 2052-4110

VL - 6

SP - 3781

EP - 3785

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 22

ER -

Exploration of 1,3-dipolar cycloaddition reactions to construct the core skeleton of Calyciphylline A-type alkaloids

Abstract

Access to Document

Other files and links

Fingerprint

Cite this