A ring expansion route to benzo substituted medium- and large-ring systems. Synthesis of trans-7,8-benzocyclododeca-5,7-dien-1-one

1977 ◽  
Vol 42 (2) ◽  
pp. 280-281 ◽  
Author(s):  
Richard W. Thies ◽  
Hae-Horng J. Shih
Keyword(s):  
Ring Expansion ◽  
Ring Systems ◽  
Large Ring

scholarly journals Synthesis of leucascandrolide A

2005 ◽  
Vol 77 (7) ◽  
pp. 1161-1169 ◽  
Author(s):  
Ying Wang ◽  
Jelena Janjic ◽  
Sergey A. Kozmin
Keyword(s):  
Growth Inhibition ◽  
Natural Product ◽  
Marine Natural Product ◽  
Yeast Cells ◽  
Leucascandrolide A ◽  
Ring Systems ◽  
Large Ring ◽  
Stereocontrolled Synthesis ◽  
Potent Growth

This paper describes a convergent and stereocontrolled synthesis of leucascandrolide A, a marine natural product that exhibits potent growth inhibition of mammalian and yeast cells. The approach features a substrate-directed relay of the stereochemical information via a series of highly diastereoselective transformations. Spontaneous macrolactolization discovered during this synthetic exercise has provided an unprecedented access to this marine macrolide and demonstrates a new tactic for assembling large-ring systems based on the thermodynamic preference of hemiacetalization.

scholarly journals Structurally diverse arene-fused ten-membered lactams accessed via hydrolytic imidazoline ring expansion

2017 ◽  
Vol 15 (14) ◽  
pp. 2906-2909 ◽  
Author(s):  
Alexander Sapegin ◽  
Angelina Osipyan ◽  
Mikhail Krasavin
Keyword(s):  
Medicinal Chemistry ◽  
Ring Expansion ◽  
Membered Ring ◽  
Synthetic Methods ◽  
Ring Systems ◽  
New Hire ◽  
Imidazoline Ring

A facile approach to hitherto unknown ten-membered ring systems via a hydrolytic imidazoline ring expansion (HIRE) is described. Medium-sized rings are scarce in the contemporary medicinal chemistry toolbox. The new HIRE strategy broadens the arsenal of synthetic methods to obtain such scaffolds.

Construction of Thienothiophene and Thienofuran Ring Systems via Ring Expansion of Difluorothiiranes Generated from Dithioesters

2021 ◽  
Author(s):  
Kohei Fuchibe ◽  
Ibuki Mukohara ◽  
Atsushi Yamada ◽  
Daisuke Miyazaki ◽  
Ryo Takayama ◽  
...  
Keyword(s):  
Ring Expansion ◽  
Ring Systems
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