Total syntheses of (−)-15-oxopuupehenol and (+)-puupehenone and formal syntheses of (−)-puupehenol and (+)-puupehedione
Literature Information
Publication Date
2019-11-15
DOI
10.1039/C9QO01027K
Impact Factor
5.281
Authors
Huayue Song, Lin Liu, Mingyang Yang, Guangmiao Wu, Peng Chen, Xingang Xie, Xuegong She
View Original
Abstract
A concise total synthesis of antitumor and antimalarial marine sponge metabolite (−)-15-oxopuupehenol has been accomplished in 8 steps (longest linear route) with an overall yield of 18% from R-(−)-carvone. Our synthesis involves a Suzuki carbonylative coupling reaction to assemble the compact tetra-substituted α,β-unsaturated aryl ketone and a KOH promoted intramolecular cyclization reaction to construct the unique chromanone core. The antituberculosis drug (+)-puupehenone is obtained via a three-step transformation from the synthetic (−)-15-oxopuupehenol. The formal syntheses of (−)-puupehenol and (+)-puupehedione can also be achieved from the same advanced intermediate 19.
Related Literature
Copper-catalyzed direct and odorless selenylation with a sodium selenite-based reagent
Yuan Cao, Jie Liu, Fanmin Liu, Lvqi Jiang, Wenbin Yi
2019-01-30
Research Article
DOI: 10.1039/C8QO01355A
Copper-mediated direct sulfonylation of C(sp2)–H bonds employing TosMIC as a sulfonyl source
Lin-Bao Zhang, Jia Liu, Xin-Qi Hao, Jun-Long Niu, Mao-Ping Song
2019-04-30
Research Article
DOI: 10.1039/C9QO00391F
Tunable enforced cavities inside self-assembled capsules‡
Takeshi Maehara, Ryo Sekiya, Kentaro Harada, Takeharu Haino
2019-01-31
Research Article
DOI: 10.1039/C9QO00010K
Fischernolides A–D, four novel diterpene-based meroterpenoid scaffolds with antitumor activities from Euphorbia fischeriana
Jun He, Yung-Chi Cheng, Pei-Cheng Zhang, Yu Yan, Hao-Jun Zhang, Wei-Ku Zhang, Jie-Kun Xu
2019-02-15
Research Article
DOI: 10.1039/C8QO01379A
19F-GEST NMR: studying dynamic interactions in host–guest systems
Liat Avram, Amnon Bar-Shir
2019-04-01
Highlight
DOI: 10.1039/C9QO00311H
Insights into the synthesis of pillar[5]arene and its conversion into pillar[6]arene
Marta Da Pian, Fabrizio Fabris, Alessandro Scarso
2019-03-06
Research Article
DOI: 10.1039/C9QO00176J
Highly efficient enantioselective synthesis of bispiro[benzofuran-oxindole-pyrrolidine]s through organocatalytic cycloaddition
Boyu Li, Fengyun Gao, Xing Feng, Mengmeng Sun, Yifei Guo, Dongwa Wen, Yabo Deng, Jinqi Huang, Kairong Wang, Wenjin Yan
2019-03-18
Research Article
DOI: 10.1039/C9QO00241C
You might also like
Compound Q&A
How should waste containing (6-Bromo-2-naphthyl)oxy](dimethyl)(2-methyl-2-propanyl)silane be handled?
Waste containing (6-Bromo-2-naphthyl)oxy](dimethyl)(2-methyl-2-propanyl)silane (...
100751-65-3[(6-Bromo-2-naphthyl...
Compound Q&A
How is 7-Fluoro-4-isoquinolinecarboxylic acid (CAS: 1841081-40-0) typically synthesized?
7-Fluoro-4-isoquinolinecarboxylic acid can be synthesized via a multi-step proce...
1841081-40-07-Fluoro-4-isoquinol...
Compound Q&A
What are the physical and chemical properties of 2,3,5,6-Tetrabromothieno[3,2-b]thiophene (CAS: 124638-53-5)?
2,3,5,6-Tetrabromothieno[3,2-b]thiophene is a crystalline compound with a high m...
124638-53-52,3,5,6-Tetrabromoth...
Compound Q&A
Is 1-[4-(Benzylamino)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-yl]-2-methyl-1H-indole-4-carboxamide (CAS: 1542705-92-9) safe?
1-[4-(Benzylamino)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-yl]-2-methyl-1H-indol...
1542705-92-91-[4-(Benzylamino)-7...
Compound Q&A
What is the market or research trend for imidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxylic acid, 3,4-dihydro-3-methyl-4-oxo- (CAS: 113942-30-6)?
The market for imidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxylic acid, 3,4-dihydro-3...
113942-30-6Imidazo[5,1-d]-1,2,3...
Compound Q&A
What is 3-(Triisopropylsilyl)propiolaldehyde (CAS: 163271-80-5)?
3-(Triisopropylsilyl)propiolaldehyde is a synthetic organic compound with the CA...
163271-80-53-(Triisopropylsilyl...
Compound Q&A
What regulatory guidelines apply to 6-Nitro-2H-1,4-benzoxazin-3(4H)-one (CAS: 81721-87-1)?
6-Nitro-2H-1,4-benzoxazin-3(4H)-one (CAS: 81721-87-1) is subject to various regu...
81721-87-16-Nitro-2H-1,4-benzo...
Compound Q&A
How should waste containing (3-Fluorophenyl)(4-{[(2-methyl-2-propanyl)oxy]carbonyl}-1-piperazinyl)acetic acid (CAS: 885272-91-3) be handled?
Waste containing (3-Fluorophenyl)(4-{[(2-methyl-2-propanyl)oxy]carbonyl}-1-piper...
885272-91-3(3-Fluorophenyl)(4-{...
Compound Q&A
What are the physical and chemical properties of N,N'-4,4'-Biphenyldiyldiisonicotinamide (CAS: 55119-40-9)?
N,N'-4,4'-Biphenyldiyldiisonicotinamide is a white crystalline solid with a mole...
55119-40-9N,N'-4,4'-Biphenyldi...
Compound Q&A
What industries use 6-Bromo-8-fluoro-2-quinazolinol (CAS: 1036756-15-6)?
6-Bromo-8-fluoro-2-quinazolinol is primarily used in the pharmaceutical industry...
1036756-15-66-Bromo-8-fluoro-2-q...
Source Journal
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
![(2S)-2-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-4-pentynoic acid structure](https://static.chemtradehub.com/structs/630/63039-48-5-b66d.webp "(2S)-2-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-4-pentynoic acid structure")
(2S)-2-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-4-pentynoic acid
CAS Number:
63039-48-5
Molecular Formula:
C10H15NO4
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.