Stereoselective total synthesis of (±)-vindeburnol and (±)-16-epi-vindeburnol

2021 ◽  
Author(s):  
Xiangtao Chen ◽  
Lei Yu ◽  
huijing Wang ◽  
Wen Zhang ◽  
Pei Tang ◽  
...  

A concise stereoselective total synthesis of (±)-vindeburnol and its epimer (±)-16-epi-vindeburnol is presented. This synthetic work features the utilization of Baeyer-Villiger oxidation to install different types of lactone substrate, and...

Tetrahedron ◽  
2009 ◽  
Vol 65 (33) ◽  
pp. 6626-6634 ◽  
Author(s):  
Olena Affolter ◽  
Angelika Baro ◽  
Wolfgang Frey ◽  
Sabine Laschat

ChemInform ◽  
2010 ◽  
Vol 30 (30) ◽  
pp. no-no
Author(s):  
Hisahiro Hagiwara ◽  
Hidenori Nagatomo ◽  
Shin-ichi Kazayama ◽  
Hitoshi Sakai ◽  
Takashi Hoshi ◽  
...  

1993 ◽  
Vol 34 (48) ◽  
pp. 7669-7672 ◽  
Author(s):  
Frederick E. Ziegler ◽  
Hakwon Kim

2013 ◽  
Vol 8 (7) ◽  
pp. 1934578X1300800
Author(s):  
Ken-ichi Sato ◽  
Shoji Akai ◽  
Juji Yoshimura

This report describes the stereocontrolled total synthesis of the multi-functionalized cyclitol derivative tetrodotoxin containing eight asymmetric carbons and different types of branched-chains from myo-inositol and D-glucose using three different methods. The tetrodotoxin derivatives possess a relatively small molecular weight but unique structural and chemical properties. Selection of the appropriate synthetic method may be useful not only for compounds related to TTX (including related derivatives) but also for other highly complex multi-functionalized cyclitols containing branched-chains.


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