Total Synthesis of Cyclosporin O Both in Solution and in the Solid Phase Using Novel Thiazolium-, Immonium-, and Pyridinium-Type Coupling Reagents:  BEMT, BDMP, and BEP1

2000 ◽  
Vol 65 (10) ◽  
pp. 2951-2958 ◽  
Author(s):  
Peng Li ◽  
Jie Cheng Xu
Keyword(s):  
Total Synthesis ◽  
Solid Phase ◽  
Coupling Reagents ◽  
Type Coupling

Solid-Phase Total Synthesis of Trunkamide A1

2001 ◽  
Vol 66 (23) ◽  
pp. 7568-7574 ◽  
Author(s):  
Josep M. Caba ◽  
Ignacio M. Rodriguez ◽  
Ignacio Manzanares ◽  
Ernest Giralt ◽  
Fernando Albericio
Keyword(s):  
Total Synthesis ◽  
Solid Phase

scholarly journals Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment

2020 ◽  
Vol 16 ◽  
pp. 670-673
Author(s):  
Jan Geldsetzer ◽  
Markus Kalesse
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Cross Coupling ◽  
Vinyl Bromide ◽  
Type Coupling ◽  
Chiral Centers

The stereoselective synthesis of the (Z)-enamide fragment of chondrochloren (1) is described. A Buchwald-type coupling between amide 3 and (Z)-bromide 4 was used to generate the required fragment. The employed amide 3 comprising three chiral centers was obtained through a seven-step sequence starting from ᴅ-ribonic acid-1,4-lactone. The (Z)-vinyl bromide 4 is accessible in four steps from 4-hydroxybenzaldehyde. The pivotal cross coupling between both fragments was achieved after extensive experimentation with copper(I) iodide, K2CO3 and N,N′-dimethylethane-1,2-diamine.

Solid-Phase Total Synthesis of Scytalidamide A

2003 ◽  
Vol 68 (23) ◽  
pp. 8774-8779 ◽  
Author(s):  
Wenxin Gu ◽  
Richard B. Silverman
Keyword(s):  
Total Synthesis ◽  
Solid Phase

Synthesis of Optically Active 15-epi-9,14-Methylene Lipoxin A4

Synthesis ◽  
2018 ◽  
Vol 50 (06) ◽  
pp. 1246-1258
Author(s):  
Udo Nubbemeyer ◽  
Adile Duymaz ◽  
Jochen Körber ◽  
Carolin Hofmann ◽  
Dorothea Gerlach
Keyword(s):  
Total Synthesis ◽  
Building Block ◽  
Building Blocks ◽  
Optically Active ◽  
Protecting Groups ◽  
Lipoxin A4 ◽  
Methylene Bridge ◽  
Type Coupling ◽  
Important Field ◽  
Gain Access

The synthesis of lipoxin A4 and B4 analogues (LXA4, LXB4) to gain access to stabilized inflammation resolving compounds is an important field of research. Starting from known structural requirements of the natural compounds displaying biological activity and a broad investigation of their rapid metabolism, various LXA4 derivatives have been developed and tested. Focusing on variation and stabilization of the conjugated E,E,Z,E C7–C14 tetraene moiety of natural LXA4, a methylene bridge introduced between C9 and C14 might suppress any Z/E isomerization of the C11–C12 olefin. Intending to enable at least known structure variations in connection with the C1–C7 and the C15–C20 fragments, a convergent total synthesis starting from a known cycloheptatriene is developed. The C1–C8 building blocks are generated via six-step ex-chiral pool sequences starting from 2-deoxy-d-ribose delivering two 5,6-dihydroxy carboxylic acid derivatives with C7 aldehyde functions. The synthesis of the C8–C21 building block starts from a known cycloheptatriene 1-carbonester (C8–C14, C21) and hexanoyl chloride (C15–C20). After Friedel–Crafts-type coupling, the defined configuration of the C15 OH group is introduced via enantioselective reduction of the ketone precursor. Following an additional four steps, an aryl sulfone C9–C21 building block is completed ready for a key Julia–Kocienski olefination with the C1–C7 compounds. Finally, removal of the protecting groups completes the synthesis of the target optically active 9,14-methylene LXA4 methyl ester.

scholarly journals Further applications of classical amide coupling reagents: Microwave-assisted esterification on solid phase

2018 ◽  
Vol 24 (8-9) ◽  
pp. e3111 ◽  
Author(s):  
Risa Takayama ◽  
Shun Hayakawa ◽  
Hiroshi Hinou ◽  
Fernando Albericio ◽  
Fayna Garcia-Martin
Keyword(s):  
Solid Phase ◽  
Coupling Reagents ◽  
Microwave Assisted ◽  
Amide Coupling

Solid‐Phase Total Synthesis of Yaku'amide B Enabled by Traceless Staudinger Ligation

2020 ◽  
Vol 59 (11) ◽  
pp. 4564-4571 ◽  
Author(s):  
Hiroaki Itoh ◽  
Kensuke Miura ◽  
Koichi Kamiya ◽  
Tomoya Yamashita ◽  
Masayuki Inoue
Keyword(s):  
Total Synthesis ◽  
Solid Phase ◽  
Staudinger Ligation
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