Asymmetric Total Synthesis of Hasubanan Alkaloids: Periglaucines A–C, N,O-Dimethyloxostephine and Oxostephabenine

Shaolei Ding; Yingbo Shi; Baochao Yang; Min Hou; Haibing He; Shuanhu Gao

doi:10.1002/anie.202214873

Asymmetric Total Synthesis of Hasubanan Alkaloids: Periglaucines A–C, N,O-Dimethyloxostephine and Oxostephabenine

Shaolei Ding
, Yingbo Shi
, Baochao Yang
, Min Hou
, Haibing He
, Shuanhu Gao^*

^*此作品的通讯作者

化学与分子工程学院

East China Normal University
Sichuan Normal University

科研成果: 期刊稿件 › 文章 › 同行评审

18 引用（Scopus）

摘要

We report herein the asymmetric total synthesis of periglaucines A–C, N,O-dimethyloxostephine and oxostephabenine. The key strategies used include: 1) a Rh^I-catalyzed regio- and diastereoselective Hayashi-Miyaura reaction to connect two necessary fragments; 2) an intramolecular photoenolization/Diels–Alder (PEDA) reaction to construct the highly functionalized tricyclic core skeleton bearing a quaternary center; 3) a bio-inspired intramolecular Michael addition and transannular acetalization to generate the aza[4.4.3]propellane and the tetrahydrofuran ring.

源语言	英语
文章编号	e202214873
期刊	Angewandte Chemie - International Edition
卷	62
期	2
DOI	https://doi.org/10.1002/anie.202214873
出版状态	已出版 - 9 1月 2023

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title = "Asymmetric Total Synthesis of Hasubanan Alkaloids: Periglaucines A–C, N,O-Dimethyloxostephine and Oxostephabenine",

abstract = "We report herein the asymmetric total synthesis of periglaucines A–C, N,O-dimethyloxostephine and oxostephabenine. The key strategies used include: 1) a RhI-catalyzed regio- and diastereoselective Hayashi-Miyaura reaction to connect two necessary fragments; 2) an intramolecular photoenolization/Diels–Alder (PEDA) reaction to construct the highly functionalized tricyclic core skeleton bearing a quaternary center; 3) a bio-inspired intramolecular Michael addition and transannular acetalization to generate the aza[4.4.3]propellane and the tetrahydrofuran ring.",

keywords = "Hasubanan Alkaloids, Natural Products, Photoenolization/Diels–Alder Reaction, Quaternary Centers, Total Synthesis",

author = "Shaolei Ding and Yingbo Shi and Baochao Yang and Min Hou and Haibing He and Shuanhu Gao",

note = "Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

year = "2023",

month = jan,

day = "9",

doi = "10.1002/anie.202214873",

language = "英语",

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TY - JOUR

T1 - Asymmetric Total Synthesis of Hasubanan Alkaloids

T2 - Periglaucines A–C, N,O-Dimethyloxostephine and Oxostephabenine

AU - Ding, Shaolei

AU - Shi, Yingbo

AU - Yang, Baochao

AU - Hou, Min

AU - He, Haibing

AU - Gao, Shuanhu

PY - 2023/1/9

Y1 - 2023/1/9

N2 - We report herein the asymmetric total synthesis of periglaucines A–C, N,O-dimethyloxostephine and oxostephabenine. The key strategies used include: 1) a RhI-catalyzed regio- and diastereoselective Hayashi-Miyaura reaction to connect two necessary fragments; 2) an intramolecular photoenolization/Diels–Alder (PEDA) reaction to construct the highly functionalized tricyclic core skeleton bearing a quaternary center; 3) a bio-inspired intramolecular Michael addition and transannular acetalization to generate the aza[4.4.3]propellane and the tetrahydrofuran ring.

AB - We report herein the asymmetric total synthesis of periglaucines A–C, N,O-dimethyloxostephine and oxostephabenine. The key strategies used include: 1) a RhI-catalyzed regio- and diastereoselective Hayashi-Miyaura reaction to connect two necessary fragments; 2) an intramolecular photoenolization/Diels–Alder (PEDA) reaction to construct the highly functionalized tricyclic core skeleton bearing a quaternary center; 3) a bio-inspired intramolecular Michael addition and transannular acetalization to generate the aza[4.4.3]propellane and the tetrahydrofuran ring.

KW - Hasubanan Alkaloids

KW - Natural Products

KW - Photoenolization/Diels–Alder Reaction

KW - Quaternary Centers

KW - Total Synthesis

UR - https://www.scopus.com/pages/publications/85143281637

U2 - 10.1002/anie.202214873

DO - 10.1002/anie.202214873

M3 - 文章

C2 - 36357322

AN - SCOPUS:85143281637

SN - 1433-7851

VL - 62

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 2

M1 - e202214873

ER -

Asymmetric Total Synthesis of Hasubanan Alkaloids: Periglaucines A–C, N,O-Dimethyloxostephine and Oxostephabenine

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