Stereoselective Synthesis of the Core Structures of Pyrrocidines and Wortmannines through the Excited-State Nazarov Reactions

Dongsheng Xue; Yonglei Que; Hao Shao; Haibing He; Xiaoli Zhao; Shuanhu Gao

doi:10.1021/acs.orglett.1c00643

Stereoselective Synthesis of the Core Structures of Pyrrocidines and Wortmannines through the Excited-State Nazarov Reactions

Dongsheng Xue, Yonglei Que, Hao Shao, Haibing He, Xiaoli Zhao, Shuanhu Gao

School of Chemistry and Molecular Engineering

East China Normal University

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

7 Scopus citations

Abstract

The reaction conditions and scope of the excited-state Nazarov reaction of dicyclicvinyl ketones were studied. The stereochemistry of this electrocyclization is consistent with the mechanism of the pericyclic reaction and Woodward-Hoffmann rule. UV-light-promoted excited-state Nazarov reactions gave hydrofluorenones bearing a syn-cis configuration via a disrotatory cyclization. The core tricyclic hydrofluorenones of pyrrocidines and wortmannines were constructed via the excited-state Nazarov reactions, which demonstrated their synthetic potential in complex natural product total synthesis.

Original language	English
Pages (from-to)	2736-2741
Number of pages	6
Journal	Organic Letters
Volume	23
Issue number	7
DOIs	https://doi.org/10.1021/acs.orglett.1c00643
State	Published - 2 Apr 2021

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10.1021/acs.orglett.1c00643

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title = "Stereoselective Synthesis of the Core Structures of Pyrrocidines and Wortmannines through the Excited-State Nazarov Reactions",

abstract = "The reaction conditions and scope of the excited-state Nazarov reaction of dicyclicvinyl ketones were studied. The stereochemistry of this electrocyclization is consistent with the mechanism of the pericyclic reaction and Woodward-Hoffmann rule. UV-light-promoted excited-state Nazarov reactions gave hydrofluorenones bearing a syn-cis configuration via a disrotatory cyclization. The core tricyclic hydrofluorenones of pyrrocidines and wortmannines were constructed via the excited-state Nazarov reactions, which demonstrated their synthetic potential in complex natural product total synthesis.",

author = "Dongsheng Xue and Yonglei Que and Hao Shao and Haibing He and Xiaoli Zhao and Shuanhu Gao",

note = "Publisher Copyright: {\textcopyright} ",

year = "2021",

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doi = "10.1021/acs.orglett.1c00643",

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T1 - Stereoselective Synthesis of the Core Structures of Pyrrocidines and Wortmannines through the Excited-State Nazarov Reactions

AU - Xue, Dongsheng

AU - Que, Yonglei

AU - Shao, Hao

AU - He, Haibing

AU - Zhao, Xiaoli

AU - Gao, Shuanhu

PY - 2021/4/2

Y1 - 2021/4/2

N2 - The reaction conditions and scope of the excited-state Nazarov reaction of dicyclicvinyl ketones were studied. The stereochemistry of this electrocyclization is consistent with the mechanism of the pericyclic reaction and Woodward-Hoffmann rule. UV-light-promoted excited-state Nazarov reactions gave hydrofluorenones bearing a syn-cis configuration via a disrotatory cyclization. The core tricyclic hydrofluorenones of pyrrocidines and wortmannines were constructed via the excited-state Nazarov reactions, which demonstrated their synthetic potential in complex natural product total synthesis.

AB - The reaction conditions and scope of the excited-state Nazarov reaction of dicyclicvinyl ketones were studied. The stereochemistry of this electrocyclization is consistent with the mechanism of the pericyclic reaction and Woodward-Hoffmann rule. UV-light-promoted excited-state Nazarov reactions gave hydrofluorenones bearing a syn-cis configuration via a disrotatory cyclization. The core tricyclic hydrofluorenones of pyrrocidines and wortmannines were constructed via the excited-state Nazarov reactions, which demonstrated their synthetic potential in complex natural product total synthesis.

UR - https://www.scopus.com/pages/publications/85103801109

U2 - 10.1021/acs.orglett.1c00643

DO - 10.1021/acs.orglett.1c00643

M3 - 文章

C2 - 33760620

AN - SCOPUS:85103801109

SN - 1523-7060

VL - 23

SP - 2736

EP - 2741

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

Stereoselective Synthesis of the Core Structures of Pyrrocidines and Wortmannines through the Excited-State Nazarov Reactions

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