Efforts toward the total synthesis of (±)-toxicodenane A utilizing an oxidopyrylium-based [5+2] cycloaddition of a silicon-tethered BOC-pyranone

被引：7

作者：

Grabowski, Jacob P. ^{[1
]}

Ferrence, Gregory M. ^{[1
]}

Mitchell, T. Andrew ^{[1
]}

机构：

[1] Illinois State Univ, Dept Chem, Campus Box 4160, Normal, IL 61790 USA

来源：

TETRAHEDRON LETTERS | 2020年 / 61卷 / 38期

基金：

美国国家科学基金会;

关键词：

Toxicodenane; Total synthesis; 5+2] cycloaddition; Oxidopyrylium; Furan; NATURAL-PRODUCTS; REARRANGEMENT; COMPLEXES; REAGENTS; UNIQUE; RESIN;

D O I：

10.1016/j.tetlet.2020.152324

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthetic efforts toward the tricyclic core of (+/-)-toxicodenane A are reported. This strategy takes advantage of the Feist-Benary furan annulation, Achmatowicz oxidative rearrangement, and oxidopyrylium-based [5+2] cycloaddition to access a key tetracyclic intermediate. This work provides a foundation that can be utilized toward the total synthesis of the natural product. (C) 2020 Elsevier Ltd. All rights reserved.

引用

页数：3

共 7 条

[1] Silicon-Tethered Intramolecular [5+2] Oxidopyrylium-Based Cycloaddition and Reductive Cleavage of Ether Bridge: Synthetic Studies Toward Arteminolides
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Mitchell, T. Andrew
[J]. TETRAHEDRON LETTERS, 2022, 107
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[5] Studies toward the synthesis of arteminolide: [5+2] cycloaddition reaction of allenes with oxidopyrylium ions
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Sohn, JH
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[J]. TETRAHEDRON LETTERS, 2001, 42 (09) : 1695 - 1698
[6] Highly stereoselective 7-membered ring synthesis based upon the oxidopyrylium-alkene [5+2]cycloaddition reaction
Ohmori, N
Miyazaki, T
Kojima, S
Ohkata, K
[J]. CHEMISTRY LETTERS, 2001, (09) : 906 - 907
[7] Asymmetric total synthesis of (+)-aphanamol I based on the transition metal catalyzed [5+2] cycloaddition of allenes and vinylcyclopropanes
Wender, PA
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[J]. ORGANIC LETTERS, 2000, 2 (15) : 2323 - 2326

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