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

School of Chemistry and Molecular Engineering

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

15 Scopus citations

Abstract

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.

Original language	English
Article number	e202214873
Journal	Angewandte Chemie - International Edition
Volume	62
Issue number	2
DOIs	https://doi.org/10.1002/anie.202214873
State	Published - 9 Jan 2023

Keywords

Hasubanan Alkaloids
Natural Products
Photoenolization/Diels–Alder Reaction
Quaternary Centers
Total Synthesis

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10.1002/anie.202214873

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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.",

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

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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

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M1 - e202214873

ER -

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

Abstract

Keywords

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