Isoxerophilins A and B, two diterpene heterodimers from Isodon xerophilus: structural elucidation and semisynthesis of isoxerophilin analogues

Literature Information

Publication Date 2023-11-07
DOI 10.1039/D3QO01679J
Impact Factor 5.281
Authors

Bing-Chao Yan, Ling-Mei Kong, Kun Hu, Xing-Ren Li, Xiao-Nian Li, Han-Dong Sun, Yan Li, Pema-Tenzin Puno


View Original

Abstract

Two types of novel diterpene heterodimers, isoxerophilins A (1, ent-kaurane–sempervirane) and B (2, ent-kaurane–abietane), were isolated from the roots of Isodon xerophilus. Their structures and absolute configurations were determined by spectroscopic data and single crystal X-ray diffraction analysis. A bioinspired semisynthesis of ten isoxerophilin analogues, featuring a tandem oxidative dearomatization/intermolecular Diels–Alder reaction, has been achieved, and the transformation of ferruginol into a sempervirane scaffold was accomplished by the SIBX-mediated tandem reaction. Compound 12 promotes MICA/B expression on SMMC-7721 cells.

Related Literature

Molecular dynamics studies of native and substituted cyclodextrins in different media: 1. Charge derivation and force field performances

Christine Cézard, Frédéric Aubry, Florence Djedaïni-Pilard, François-Yves Dupradeau

2011-07-26 Paper

DOI: 10.1039/C1CP20854C

Polarization induced water molecule dissociation below the first-order electronic-phase transition temperature

Andrew Das Arulsamy, Zlatko Kregar, Kristina Eleršič, Martina Modic, Uma Shankar Subramani

2011-07-21 Paper

DOI: 10.1039/C1CP20138G

Graphical prediction of quantum interference-induced transmission nodes in functionalized organic molecules

Troels Markussen, Robert Stadler, Kristian S. Thygesen

2011-06-28 Paper

DOI: 10.1039/C1CP20924H

The protein folding transition-state ensemble from a Gō-like model

Athi N. Naganathan

2011-07-21 Paper

DOI: 10.1039/C1CP20964G

Structural characterization and DFT study of VIVO(acac)2 in imidazolium ionic liquids

Andreia Mota, Jason P. Hallett, Maxim L. Kuznetsov, Isabel Correia

2011-07-25 Paper

DOI: 10.1039/C1CP20800D

Inside front cover

Front/Back Matter

DOI: 10.1039/C1CP90122B

Quantum design rules for single molecule logic gates

N. Renaud, M. Hliwa, C. Joachim

2011-07-27 Paper

DOI: 10.1039/C1CP21221D

Contents

Front/Back Matter

DOI: 10.1039/C1CP90099D

μ-XAFS of a single particle of a practical NiOx/Ce2Zr2Oy catalyst

Tomoya Uruga, Hajime Tanida, Yasuko Terada, Yasuhiro Iwasawa, Shin-ichi Ohkoshi

2011-06-08 Communication

DOI: 10.1039/C1CP20895K

Stabilization of organic field-effect transistors by tert-butyl groups in dibenzotetrathiafulvalene derivatives

Junki Nagakubo, Minoru Ashizawa, Tadashi Kawamoto, Akihiko Tanioka

2011-06-15 Paper

DOI: 10.1039/C1CP21507H

You might also like

Compound Q&A

How should 2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) be stored?

2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) should be stored in ...

615-45-22-Methylbenzene-1,4-...
Compound Q&A

Is (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide (CAS: 132747-20-7) safe?

(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide is generally considered sa...

132747-20-7(1S,4S)-2,5-Diazabic...
Compound Q&A

What industries use (6-Chloropyridazin-3-YL)methanamine (CAS: 871826-15-2)?

(6-Chloropyridazin-3-YL)methanamine finds applications in the pharmaceutical ind...

871826-15-2(6-Chloropyridazin-3...
Compound Q&A

What are the main uses of 2-Fluoro-3-methylphenol (CAS: 77772-72-6)?

2-Fluoro-3-methylphenol is primarily used in the synthesis of pharmaceuticals, p...

77772-72-62-Fluoro-3-methylphe...
Compound Q&A

What precautions should be taken when handling 3-Methoxy-4-nitrobenzonitrile (CAS: 177476-75-4)?

When handling 3-Methoxy-4-nitrobenzonitrile, it is important to wear appropriate...

177476-75-43-Methoxy-4-nitroben...
Compound Q&A

What precautions should be taken when handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4)?

When handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4), it is ...

211949-57-4[1,3]Oxazolo[4,5-b]p...
Compound Q&A

What regulatory guidelines apply to 4-Ethynylbenzamide (CAS: 90347-86-7)?

4-Ethynylbenzamide (CAS: 90347-86-7) falls under various regulatory guidelines i...

90347-86-74-Ethynylbenzamide
Compound Q&A

What are the main uses of 3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone (CAS: 186822-57-1)?

3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone is primarily used as an intermediat...

186822-57-13-(2-Ethylphenyl)-2-...
Compound Q&A

What is (2-Fluoro-6-methoxyphenyl)acetic acid (CAS: 500912-19-6)?

(2-Fluoro-6-methoxyphenyl)acetic acid, also known as 4-fluoro-3-methoxybenzoic a...

500912-19-6(2-Fluoro-6-methoxyp...
Compound Q&A

What is the market or research trend for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9)?

Market trends for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9) indicat...

102196-18-92-[4-(Hydroxymethyl)...

Source Journal

Organic Chemistry Frontiers

Organic Chemistry Frontiers
CiteScore: 7.8
Self-citation Rate: 8.7%
Articles per Year: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.