Asymmetric Total Synthesis of (−)-Merrilactone A: Use of a Bulky Protecting Group as Long-Range Stereocontrolling Element

2006 ◽  
Vol 45 (29) ◽  
pp. 4843-4848 ◽  
Author(s):  
Masayuki Inoue ◽  
Takaaki Sato ◽  
Masahiro Hirama
Keyword(s):  
Total Synthesis ◽  
Long Range ◽  
Protecting Group ◽  
Asymmetric Total Synthesis ◽  
Merrilactone A

Asymmetric Total Synthesis of Heronamides A-C: Stereochemical Confirmation and Impact of Long-Range Stereochemical Communication on the Biological Activity

2016 ◽  
Vol 22 (25) ◽  
pp. 8586-8595 ◽  
Author(s):  
Naoki Kanoh ◽  
Shunya Itoh ◽  
Kohei Fujita ◽  
Kohei Sakanishi ◽  
Ryosuke Sugiyama ◽  
...  
Keyword(s):  
Biological Activity ◽  
Total Synthesis ◽  
Long Range ◽  
Asymmetric Total Synthesis

Total Synthesis of Merrilactone A: Long-Range Stereocontrol and Asymmetric Desymmetrization

ChemInform ◽  
2007 ◽  
Vol 38 (41) ◽  
Author(s):  
Masayuki Inoue ◽  
Takaaki Sato ◽  
Masahiro Hirama
Keyword(s):  
Total Synthesis ◽  
Long Range ◽  
Merrilactone A

A protecting group free and scalable approach towards total synthesis of (−)-venlafaxine

RSC Advances ◽  
2014 ◽  
Vol 4 (28) ◽  
pp. 14468-14470 ◽  
Author(s):  
Subhash P. Chavan ◽  
Kailash P. Pawar ◽  
Sumanta Garai
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Epoxide Ring ◽  
Protecting Group ◽  
Asymmetric Total Synthesis ◽  
Epoxide Ring Opening ◽  
Key Steps

A protecting group free asymmetric total synthesis of (−)-venlafaxine is reported. The strategy employs Sharpless epoxidation and regio-selective epoxide ring opening by an in situ generated Gilman reagent as key steps. This paper reports a 53% overall yield in 6 steps for total synthesis of (−)-venlafaxine.

Protecting-group-free catalytic asymmetric total synthesis of (−)-rosmarinecine

Tetrahedron ◽  
2012 ◽  
Vol 68 (36) ◽  
pp. 7295-7301 ◽  
Author(s):  
Hiroyuki Nemoto ◽  
Kouichi Tanimoto ◽  
Yukiko Kanao ◽  
Sohei Omura ◽  
Yasuyuki Kita ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Protecting Group ◽  
Asymmetric Total Synthesis ◽  
Catalytic Asymmetric

Short Protecting Group-free Syntheses of CDE Synthon of Racemic Camptothecin

2020 ◽  
Vol 17 (7) ◽  
pp. 588-591
Author(s):  
Pingxuan Shao ◽  
Wei Lu ◽  
Lei Wang
Keyword(s):  
Total Synthesis ◽  
Future Development ◽  
Protecting Group ◽  
Short Route ◽  
The Future ◽  
Tricyclic Ketone

A practical and concise total synthesis of tricyclic ketone 7 (CDE ring), a valuable intermediate for the synthesis of racemic camptothecin and analogs, was described (8 chemical steps and 29% overall yield). The synthesis starts with two inexpensive, readily available materials and is operationally simple to perform. It is worth mentioning that the reported protecting group-free synthesis, with advantages of a short route, would be helpful for the future development of industry-scale syntheses of camptothecin-family alkaloids.

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