A Unified Strategy to Construct the Tetracyclic Ring of Calyciphylline A Alkaloids: Total Synthesis of Himalensine A

Jiaxin Zhong; Kuanwei Chen; Yuanyou Qiu; Haibing He; Shuanhu Gao

doi:10.1021/acs.orglett.9b01184

A Unified Strategy to Construct the Tetracyclic Ring of Calyciphylline A Alkaloids: Total Synthesis of Himalensine A

Jiaxin Zhong
, Kuanwei Chen
, Yuanyou Qiu
, 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

67 Scopus citations

Abstract

The synthetic approach to the core framework of the calyciphylline A-type Daphniphyllum alkaloids and total synthesis of himalensine A were described herein. Nitrone-induced 1,3-dipolar [3 + 2] cycloaddition was applied for the construction of A/C rings along with the all-carbon quaternary center. Pd-catalyzed enolate alkenylation and ring closing metathesis (RCM) were adopted to install the B/D rings to accomplish the [6,6,5,7] core framework. Nazarov reaction was utilized to install the F ring to complete the total synthesis of himalensine A.

Original language	English
Pages (from-to)	3741-3745
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.9b01184
State	Published - 17 May 2019

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title = "A Unified Strategy to Construct the Tetracyclic Ring of Calyciphylline A Alkaloids: Total Synthesis of Himalensine A",

abstract = "The synthetic approach to the core framework of the calyciphylline A-type Daphniphyllum alkaloids and total synthesis of himalensine A were described herein. Nitrone-induced 1,3-dipolar [3 + 2] cycloaddition was applied for the construction of A/C rings along with the all-carbon quaternary center. Pd-catalyzed enolate alkenylation and ring closing metathesis (RCM) were adopted to install the B/D rings to accomplish the [6,6,5,7] core framework. Nazarov reaction was utilized to install the F ring to complete the total synthesis of himalensine A.",

author = "Jiaxin Zhong and Kuanwei Chen and Yuanyou Qiu and Haibing He and Shuanhu Gao",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

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doi = "10.1021/acs.orglett.9b01184",

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T1 - A Unified Strategy to Construct the Tetracyclic Ring of Calyciphylline A Alkaloids

T2 - Total Synthesis of Himalensine A

AU - Zhong, Jiaxin

AU - Chen, Kuanwei

AU - Qiu, Yuanyou

AU - He, Haibing

AU - Gao, Shuanhu

PY - 2019/5/17

Y1 - 2019/5/17

N2 - The synthetic approach to the core framework of the calyciphylline A-type Daphniphyllum alkaloids and total synthesis of himalensine A were described herein. Nitrone-induced 1,3-dipolar [3 + 2] cycloaddition was applied for the construction of A/C rings along with the all-carbon quaternary center. Pd-catalyzed enolate alkenylation and ring closing metathesis (RCM) were adopted to install the B/D rings to accomplish the [6,6,5,7] core framework. Nazarov reaction was utilized to install the F ring to complete the total synthesis of himalensine A.

AB - The synthetic approach to the core framework of the calyciphylline A-type Daphniphyllum alkaloids and total synthesis of himalensine A were described herein. Nitrone-induced 1,3-dipolar [3 + 2] cycloaddition was applied for the construction of A/C rings along with the all-carbon quaternary center. Pd-catalyzed enolate alkenylation and ring closing metathesis (RCM) were adopted to install the B/D rings to accomplish the [6,6,5,7] core framework. Nazarov reaction was utilized to install the F ring to complete the total synthesis of himalensine A.

UR - https://www.scopus.com/pages/publications/85065814854

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DO - 10.1021/acs.orglett.9b01184

M3 - 文章

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AN - SCOPUS:85065814854

SN - 1523-7060

VL - 21

SP - 3741

EP - 3745

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

A Unified Strategy to Construct the Tetracyclic Ring of Calyciphylline A Alkaloids: Total Synthesis of Himalensine A

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