Total synthesis of complex alkaloids by nucleophilic addition to amides

2018 ◽  
Vol 16 (21) ◽  
pp. 3864-3875 ◽  
Author(s):  
Takaaki Sato ◽  
Makoto Yoritate ◽  
Hayato Tajima ◽  
Noritaka Chida
Keyword(s):  
Total Synthesis ◽  
Nucleophilic Addition ◽  
Recent Progress ◽  
Nucleophilic Additions ◽  
Tertiary Amides ◽  
Secondary Amides

This mini review focuses on the recent progress of total synthesis of complex alkaloids based on the nucleophilic additions toN-alkoxyamides, tertiary amides and secondary amides.

Chemoselective Reductive Nucleophilic Addition to Tertiary Amides, Secondary Amides, andN-Methoxyamides

2014 ◽  
Vol 20 (52) ◽  
pp. 17565-17571 ◽  
Author(s):  
Minami Nakajima ◽  
Yukiko Oda ◽  
Takamasa Wada ◽  
Ryo Minamikawa ◽  
Kenji Shirokane ◽  
...  
Keyword(s):  
Nucleophilic Addition ◽  
Tertiary Amides ◽  
Secondary Amides

ChemInform Abstract: Chemoselective Reductive Nucleophilic Addition to Tertiary Amides, Secondary Amides, and N-Methoxyamides.

ChemInform ◽  
2015 ◽  
Vol 46 (22) ◽  
pp. no-no
Author(s):  
Minami Nakajima ◽  
Yukiko Oda ◽  
Takamasa Wada ◽  
Ryo Minamikawa ◽  
Kenji Shirokane ◽  
...  
Keyword(s):  
Nucleophilic Addition ◽  
Tertiary Amides ◽  
Secondary Amides

Recent Progress in Chemosensors Using Aldehyde-bearing Fluorophores for the Detection of Specific Analytes and their Bioimaging

2019 ◽  
Vol 26 (21) ◽  
pp. 4003-4028 ◽  
Author(s):  
Fangjun Huo ◽  
Yaqiong Zhang ◽  
Caixia Yin
Keyword(s):  
Biomedical Research ◽  
Nucleophilic Addition ◽  
Recent Progress ◽  
Biological Imaging ◽  
Tissue Imaging ◽  
Fluorescence Probes ◽  
Biological Applications ◽  
Convenient Procedure ◽  
Nucleophilic Mechanism

In recent years, aldehyde-appended fluorescence probes have attracted increasing attention. Fluorescent biological imaging includes many modern applications for cell and tissue imaging in biomedical research. Meanwhile, the nucleophilic mechanism is a very simple and convenient procedure for the preparation of aldehyde-sensing probes. This tutorial review focuses on aldehyde-bearing chemosensors based on nucleophilic addition mechanism with biological applications.

scholarly journals Non-Enzymatic Desymmetrization Reactions in Aqueous Media

Symmetry ◽  
2021 ◽  
Vol 13 (4) ◽  
pp. 720
Author(s):  
Satomi Niwayama
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Functional Groups ◽  
Organic Compounds ◽  
Recent Progress ◽  
Aqueous Media ◽  
Building Blocks ◽  
Organic Reactions ◽  
Environmentally Benign ◽  
Enzymatic Desymmetrization

Symmetric organic compounds are generally obtained inexpensively, and therefore they can be attractive building blocks for the total synthesis of various pharmaceuticals and natural products. The drawback is that discriminating the identical functional groups in the symmetric compounds is difficult. Water is the most environmentally benign and inexpensive solvent. However, successful organic reactions in water are rather limited due to the hydrophobicity of organic compounds in general. Therefore, desymmetrization reactions in aqueous media are expected to offer versatile strategies for the synthesis of a variety of significant organic compounds. This review focuses on the recent progress of desymmetrization reactions of symmetric organic compounds in aqueous media without utilizing enzymes.

scholarly journals Recent progress toward synthesis of chlorosulfolipids: total synthesis and methodology

2014 ◽  
Vol 55 (19) ◽  
pp. 3003-3012 ◽  
Author(s):  
Taiki Umezawa ◽  
Fuyuhiko Matsuda
Keyword(s):  
Total Synthesis ◽  
Recent Progress

Toward the total synthesis of lophotoxin — New methodologies and synthetic strategies

2006 ◽  
Vol 84 (10) ◽  
pp. 1226-1241 ◽  
Author(s):  
Peter Wipf ◽  
Michel Grenon
Keyword(s):  
Transition Metal ◽  
Total Synthesis ◽  
Recent Progress ◽  
Furan Ring ◽  
Addition Reaction ◽  
Thermal Conditions ◽  
Preliminary Results ◽  
Keto Esters ◽  
New Methodologies ◽  
Metal Catalyzed

Our recent progress toward the synthesis of the furanocembranolide lophotoxin (1) is disclosed. Strategies for the stereoselective incorporation of the C13 stereocenter by a catalytic desymmetrization of a cyclic meso-anhydride, as well as a novel 1,6-addition reaction of organocuprates to unsaturated [1,3]dioxin-4-ones are discussed. Preliminary results on the development of a rhodium-catalyzed asymmetric 1,6-addition reaction are also mentioned. Finally, modifications of a previously reported transition-metal-catalyzed cyclization reaction involving α-propargyl β-keto esters allow furan ring formation either under thermal conditions or by microwave irradiation.Key words: 1,6-addition, organocuprates, catalytic desymmetrization, furan cyclization, microwave.

ChemInform Abstract: Recent Progress in Isolation, Bioactivity Evaluation and Total Synthesis of Diarylheptanoids.

ChemInform ◽  
2001 ◽  
Vol 32 (9) ◽  
pp. no-no
Author(s):  
Jieping Zhu ◽  
G. Islas-Gonzalez ◽  
M. Bois-Choussy
Keyword(s):  
Total Synthesis ◽  
Recent Progress

Bioinspired Total Synthesis of Marine Anti-Cancer Meroterpenoids Dysideanone B and Dysiherbol A and Structure Revision of Dysiherbol A

Synlett ◽  
2021 ◽  
Author(s):  
Zhaoyong Lu ◽  
Chuanke Chong
Keyword(s):  
Total Synthesis ◽  
Heck Reaction ◽  
Recent Progress ◽  
Benzyl Bromide ◽  
Radical Cyclization ◽  
Ethoxy Group ◽  
Anti Cancer ◽  
Structure Revision ◽  
A Site ◽  
Intramolecular Heck Reaction

Our recent progress on the total synthesis of marine anti-cancer sesquiterpene quinone/hydroquinone dysideanone B and dysiherbol A was briefly highlighted. This success relied on some key transformations. The union of the terpene and quinone/hydroquinone moieties was realized through a site and stereoselective α-position alkylation of Wieland–Miescher ketone derivative with a bulky benzyl bromide. The 6/6/6/6-tetracycle of dysideanone B was constructed using an intramolecular radical cyclization and the 6/6/5/6-fused core structure of dysiherbol A was forged by an intramolecular Heck reaction, respectively. The possible origin of ethoxy group in dysideanone B was revealed by mimicking the isolation conditions at a late-stage. The structure of dysiherbol A was revised through the total synthesis of this natural product. Schmalz’s synthesis of dysiherbol A was also included.

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