Studies towards the synthesis of the functionalized C3–C14 decalin framework of alchivemycin A
Literature Information
Publication Date
2015-12-21
DOI
10.1039/C5QO00343A
Impact Factor
5.281
Authors
Shaoqiang Yang, Xiaofei Li
View Original
Abstract
We report our synthetic studies towards the synthesis of the C3–C14 fragment of alchivemycin A. The synthesis featured an asymmetric alkylation with excellent diastereoselectivity and a one-pot Julia–Kocienski olefination with excellent E-selectivity. An intramolecular Diels–Alder reaction was employed to construct the highly functionalized cis-decalin framework. Interestingly, the stereochemical outcome was not expected to generate the two stereoisomers 20 and 21 instead of the desired cis-decalin 5. The detailed mechanism of this transformation was discussed. These synthetic endeavors have offered us a number of crucial insights for the synthesis of the complex natural product alchivemycin A.
Related Literature
Structure related transport properties and cellular uptake of hyperbranched polyglycerol sulfates with hydrophobic cores
Florian Paulus, Dirk Steinhilber, Pia Welker, Dorothea Mangoldt, Kai Licha, Harald Depner, Stephan Sigrist, Rainer Haag
2014-05-15
Paper
DOI: 10.1039/C4PY00430B
Synthesis and chiral recognition ability of helical polyacetylenes bearing helicene pendants
Hiroki Iida, Tomoko Yamaguchi, Koutarou Hayashi, Daisuke Kumano, Jeanne Crassous, Nicolas Vanthuyne, Christian Roussel, Eiji Yashima
2014-06-09
Paper
DOI: 10.1039/C4PY00692E
New thermal-responsive polymers based on alanine and (meth)acryl amides
Deyang Yu, Chunhui Luo, Wenxin Fu, Zhibo Li
2014-04-28
Paper
DOI: 10.1039/C4PY00480A
From glycidyl carbonate to hydroxyurethane side-groups in alternating fluorinated copolymers
Roukaya Hamiye, Ali Alaaeddine, Mouhamad Awada, Benjamin Campagne, Sylvain Caillol, Sophie M. Guillaume, Bruno Ameduri, Jean-François Carpentier
2014-05-09
Paper
DOI: 10.1039/C4PY00547C
Synthesis and self-assembly of a novel fluorinated triphilic block copolymer
Xinxin Li, Yanhua Yang, Guojun Li
2014-04-22
Paper
DOI: 10.1039/C4PY00308J
Synthesis and characterization of isosorbide-based polyphosphonates as biobased flame-retardants
Timothy C. Mauldin, Jeffrey W. Gilman, John R. Shields, Dylan J. Boday
2014-06-02
Paper
DOI: 10.1039/C4PY00591K
Mesogen-jacketed liquid crystalline polymers with peripheral oligo(ethylene oxide) chains: phase structure and thermoresponsive behavior
Qian Tan, Junqiu Liao, Sheng Chen, Ya Zhu, Hailiang Zhang
2014-05-09
Paper
DOI: 10.1039/C4PY00371C
Switch on/off microcapsules for controllable photosensitive drug release in a ‘release-cease-recommence’ mode
Hang Lin, Wang Xiao, Si-Yong Qin, Si-Xue Cheng, Xian-Zheng Zhang
2014-05-15
Communication
DOI: 10.1039/C4PY00564C
Phosphazene-catalyzed ring-opening polymerization of ε-caprolactone: influence of solvents and initiators
Haleema Alamri, Junpeng Zhao, David Pahovnik, Nikos Hadjichristidis
2014-05-30
Paper
DOI: 10.1039/C4PY00493K
You might also like
Compound Q&A
What is Ethyl 3-cyclohexylpropanoate (CAS: 10094-36-7)?
Ethyl 3-cyclohexylpropanoate is a clear, colorless to light yellow liquid with a...
10094-36-7Ethyl 3-cyclohexylpr...
Compound Q&A
How should waste containing 2-(Hydroxymethyl)-5-(methoxycarbonyl)-6-methyl-4-(2-nitrophenyl)nicotinic acid (CAS: 34783-31-8) be handled?
Waste containing 2-(Hydroxymethyl)-5-(methoxycarbonyl)-6-methyl-4-(2-nitrophenyl...
34783-31-82-(Hydroxymethyl)-5-...
Compound Q&A
How should waste containing 2,4,6-Tris(pentafluoroethyl)-1,3,5-triazine (CAS: 858-46-8) be handled?
Waste containing 2,4,6-Tris(pentafluoroethyl)-1,3,5-triazine (CAS: 858-46-8) sho...
858-46-82,4,6-Tris(pentafluo...
Compound Q&A
What precautions should be taken when handling Chloroac-nle-oh (CAS: 56787-36-1)?
When handling Chloroac-nle-oh (CAS: 56787-36-1), it is essential to wear appropr...
56787-36-1Chloroac-nle-oh
Compound Q&A
What industries use Ethyl 6-phenylimidazo[2,1-b][1,3]thiazole-3-carboxylate (CAS: 752244-05-6)?
Ethyl 6-phenylimidazo[2,1-b][1,3]thiazole-3-carboxylate is primarily used in the...
752244-05-6Ethyl 6-phenylimidaz...
Compound Q&A
Are there alternatives to alpha-(2-Bromophenyl)benzylamine (CAS: 55095-15-3) in synthesis?
Alternatives to alpha-(2-Bromophenyl)benzylamine (CAS: 55095-15-3) in synthesis ...
55095-15-3alpha-(2-Bromophenyl...
Compound Q&A
How should waste containing 2-Chloro-5-methoxypyridine (CAS: 139585-48-1) be handled?
Waste containing 2-Chloro-5-methoxypyridine (CAS: 139585-48-1) should be managed...
139585-48-12-Chloro-5-methoxypy...
Compound Q&A
What industries use 1-(4-Methoxyphenyl)-2,5-dimethyl-1H-pyrrole (CAS: 5044-27-9)?
1-(4-Methoxyphenyl)-2,5-dimethyl-1H-pyrrole (CAS: 5044-27-9) is used in various ...
5044-27-91-(4-Methoxyphenyl)-...
Compound Q&A
Are there alternatives to 3-Bromo-5-(N-Boc)aminomethylisoxazole (CAS: 903131-45-3) in synthesis?
There are alternative reagents and compounds that can be used in the synthesis o...
903131-45-33-Bromo-5-(N-Boc)ami...
Compound Q&A
What is Tungsten(IV) oxide (CAS: 12036-22-5)?
Tungsten(IV) oxide, also known as tungsten dioxide, is a chemical compound with ...
12036-22-5Tungsten(IV) oxide
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
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.