A Biomimetic Approach to Taxol: Stereoselective Synthesis of a 12-Membered Ring Ene-Epoxide

1997 ◽  
Vol 37 (1) ◽  
pp. 31-37 ◽  
Author(s):  
Takashi Takahashi ◽  
Tadashi Okabe ◽  
Hajime Iwamoto ◽  
Yoichiro Hirose ◽  
Haruo Yamada ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Membered Ring ◽  
Biomimetic Approach

Biomimetic Approach to the Stereoselective Synthesis of Acetogenins

ChemInform ◽  
2003 ◽  
Vol 34 (42) ◽  
Author(s):  
Romano V. A. Orru ◽  
Bas Groenendaal ◽  
Jeroen van Heyst ◽  
Mark Hunting ◽  
Claudia Wesseling ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Biomimetic Approach

Towards the Total Synthesis of Schisandrene: Stereoselective Synthesis of the Dibenzocyclooctadiene Lignan Core

Synlett ◽  
2018 ◽  
Vol 29 (07) ◽  
pp. 908-911 ◽  
Author(s):  
K. Babu ◽  
Arramshetti Venkanna ◽  
Borra Poornima ◽  
Bandi Siva ◽  
B. Babu
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Asymmetric Reduction ◽  
Cross Coupling ◽  
Membered Ring ◽  
Stille Reaction ◽  
Reaction Sequence ◽  
Ring Closing Metathesis ◽  
Synthetic Strategy ◽  
First Time

A stereoselective synthesis of the dibenzocyclooctadiene ­lignan core of the natural product schisandrene is described. Starting from readily available gallic acid, the synthetic strategy involves Suzuki–Miyaura cross-coupling, Stille reaction, and ring-closing metathesis (RCM) in the reaction sequence. The required asymmetric center at C-7′ was established by an asymmetric reduction of a keto compound using the Corey–Bakshi–Shibata (CBS) catalyst. In our approach, the eight-membered ring was achieved by RCM for the first time.

Biomimetic approach toward the stereoselective synthesis of acetogenins

2003 ◽  
Vol 75 (2-3) ◽  
pp. 259-264 ◽  
Author(s):  
R. V. A. Orru ◽  
Bas Groenendaal ◽  
J. van Heyst ◽  
Mark Hunting ◽  
C. Wesseling ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Broad Spectrum ◽  
Stereoselective Synthesis ◽  
Biological Activities ◽  
Building Blocks ◽  
Hydrocarbon Chain ◽  
Tropical Trees ◽  
Asymmetric Total Synthesis ◽  
Biomimetic Approach

Acetogenins isolated from the Annonaceae family of tropical trees have drawn considerable attention owing to their broad spectrum of biological activities. They are structurally characterized by the presence of one to three tetrahydrofuran rings in the center of a long (partly hydroxylated) hydrocarbon chain that ends in a (functionalized) butenolide moiety. Here we describe some of our results toward the first asymmetric total synthesis of cis-gigantrionenin, a principal acetogenin. In this approach, an enzyme-catalyzed epoxide hydrolysis and an enzyme-triggered double cyclization are crucial and give stereoselective access to essential chiral building blocks.

Radical Abstraction vs Cyclisation in Reactions of ortho-Bromophenyl Sulfone Systems: Stereoselective Synthesis of Benz-fused Six and Seven-Membered Ring Sulfones

Synlett ◽  
1995 ◽  
Vol 1995 (09) ◽  
pp. 943-944 ◽  
Author(s):  
Christopher D. S. Brown ◽  
Allan P. Dishington ◽  
Oleg Shishkin ◽  
Nigel S. Simpkins
Keyword(s):  
Stereoselective Synthesis ◽  
Membered Ring

scholarly journals Stereoselective synthesis of three-membered ring compounds via ylide routes

1999 ◽  
Vol 71 (3) ◽  
pp. 369-376 ◽  
Author(s):  
L.-X. Dai ◽  
X.-L. Hou ◽  
Y.-G. Zhou
Keyword(s):  
Stereoselective Synthesis ◽  
Membered Ring ◽  
Ring Compounds
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