Asymmetric synthesis of tricyclic-cyclobutane by means of enantioselective deprotonation and intramolecular Michael–aldol reaction

2001 ◽  
Vol 42 (48) ◽  
pp. 8489-8491 ◽  
Author(s):  
Kiyosei Takasu ◽  
Keiko Misawa ◽  
Masataka Ihara
Keyword(s):  
Asymmetric Synthesis ◽  
Aldol Reaction ◽  
Enantioselective Deprotonation

scholarly journals Asymmetric Synthesis of the C15–C32 Fragment of Alotamide and Determination of the Relative Stereochemistry

Marine Drugs ◽  
2018 ◽  
Vol 16 (11) ◽  
pp. 414 ◽  
Author(s):  
Hao-yun Shi ◽  
Yang Xie ◽  
Pei Hu ◽  
Zi-qiong Guo ◽  
Yi-hong Lu ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Nmr Spectra ◽  
Calcium Influx ◽  
Aldol Reaction ◽  
13C Nmr Spectra ◽  
Marine Cyanobacterium ◽  
Relative Stereochemistry ◽  
Key Steps ◽  
Relative Structure

Alotamide is a cyclic depsipetide isolated from a marine cyanobacterium and possesses a unique activation of calcium influx in murine cerebrocortical neurons (EC50 4.18 µM). Due to its limited source, the three stereocenters (C19, C28, and C30) in its polyketide fragment remain undetermined. In this study, the first asymmetric synthesis of its polyketide fragment was achieved. Four relative possible diastereomers were constructed with a boron-mediated enantioselective aldol reaction and Julia–Kocienski olefination as the key steps. Comparison of 13C NMR spectra revealed the relative structure of fragment C15–C32 of alotamide.

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