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Literature DB >> 12182611

Biomimetic cycloaddition approach to tropolone natural products via a tropolone ortho-quinone methide.

Robert M Adlington¹, Jack E Baldwin, Alexander V W Mayweg, Gareth J Pritchard.

Abstract

[reaction: see text] A study toward a possible biomimetic hetero Diels-Alder reaction is reported between humulene and a novel tropolone ortho-quinone methide. A suitable tropolone ortho-quinone methide precursor has been prepared from 3-methyl-2-furoate. Heating the ortho-quinone methide precursor gave a tropolone ortho-quinone methide, which in the presence of humulene underwent a hetero Diels-Alder reaction to give a deoxy analogue of epolone B.

Entities: Chemical

Mesh：

Substances：

Year: 2002 PMID： 12182611 DOI： 10.1021/ol026467r

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

14 in total

1. Triflic acid-mediated rearrangements of 3-methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones: synthesis of methoxytropolones and furans.

Authors: Yvonne D Williams; Christine Meck; Noushad Mohd; Ryan P Murelli
Journal: J Org Chem Date: 2013-11-14 Impact factor: 4.354

2. Enzymatic Intermolecular Hetero-Diels-Alder Reaction in the Biosynthesis of Tropolonic Sesquiterpenes.

Authors: Qibin Chen; Jie Gao; Cooper Jamieson; Jiawang Liu; Masao Ohashi; Jian Bai; Daojian Yan; Bingyu Liu; Yongsheng Che; Yanan Wang; K N Houk; Youcai Hu
Journal: J Am Chem Soc Date: 2019-09-03 Impact factor: 15.419

3. Traceless Solid-Phase α-Hydroxytropolone Synthesis.

Authors: Michael P D'Erasmo; Takashi Masaoka; Jennifer A Wilson; Errol M Hunte; John A Beutler; Stuart F J Le Grice; Ryan P Murelli
Journal: Medchemcomm Date: 2016-07-07 Impact factor: 3.597

4. Synthesis of Naturally Occurring Tropones and Tropolones.

Authors: Na Liu; Wangze Song; Casi M Schienebeck; Min Zhang; Weiping Tang
Journal: Tetrahedron Date: 2014-12-09 Impact factor: 2.457

5. Maltol- and Allomaltol-Derived Oxidopyrylium Ylides: Methyl Substitution Pattern Kinetically Influences [5 + 3] Dimerization versus [5 + 2] Cycloaddition Reactions.

Authors: Lauren P Bejcek; Aswin K Garimallaprabhakaran; Duygu M Suyabatmaz; Alexander Greer; William H Hersh; Edyta M Greer; Ryan P Murelli
Journal: J Org Chem Date: 2019-10-25 Impact factor: 4.354

Biomimetic cycloaddition approach to tropolone natural products via a tropolone ortho-quinone methide.

1. Triflic acid-mediated rearrangements of 3-methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones: synthesis of methoxytropolones and furans.

2. Enzymatic Intermolecular Hetero-Diels-Alder Reaction in the Biosynthesis of Tropolonic Sesquiterpenes.

3. Traceless Solid-Phase α-Hydroxytropolone Synthesis.

4. Synthesis of Naturally Occurring Tropones and Tropolones.

5. Maltol- and Allomaltol-Derived Oxidopyrylium Ylides: Methyl Substitution Pattern Kinetically Influences [5 + 3] Dimerization versus [5 + 2] Cycloaddition Reactions.

6. Discovery and Development of a Three-Component Oxidopyrylium [5 + 2] Cycloaddition.

7. An oxidopyrylium cyclization/ring-opening route to polysubstituted α-hydroxytropolones.

8. Synthesis of a highly functionalized core of verrillin.

9. Oxidopyrylium [5+2] Cycloaddition Chemistry: Historical Perspective and Recent Advances (2008-2018).

10. The biology and synthesis of α-hydroxytropolones.