Asymmetric total synthesis of (+)-negamycin and (-)-3-epinegamycin via enantioselective 1,3-dipolar cycloaddition

1989 ◽  
Vol 54 (9) ◽  
pp. 2225-2233 ◽  
Author(s):  
Katsura Kasahara ◽  
Hideo Iida ◽  
Chihiro Kibayashi
Keyword(s):  
Total Synthesis ◽  
Dipolar Cycloaddition ◽  
Asymmetric Total Synthesis

scholarly journals Facile generation of bridged medium-sized polycyclic systems by rhodium-catalysed intramolecular (3+2) dipolar cycloadditions

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Bao-Long Hou ◽  
Jonathan J. Wong ◽  
Na Lv ◽  
Yong-Qiang Wang ◽  
K. N. Houk ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Single Step ◽  
Bioactive Molecules ◽  
Dipolar Cycloaddition ◽  
General Strategy ◽  
Diastereoselective Synthesis ◽  
Asymmetric Total Synthesis ◽  
Ring Systems ◽  
Dipolar Cycloadditions ◽  
Unusual Type

AbstractBridged medium-sized bicyclo[m.n.2] ring systems are common in natural products and potent pharmaceuticals, and pose a great synthetic challenge. Chemistry for making bicyclo[m.n.2] ring systems remains underdeveloped. Currently, there are no general reactions available for the single-step synthesis of various bridged bicyclo[m.n.2] ring systems from acyclic precursors. Here, we report an unusual type II intramolecular (3+2) dipolar cycloaddition strategy for the syntheses of various bridged bicyclo[m.n.2] ring systems. This rhodium-catalysed cascade reaction provides a relatively general strategy for the direct and efficient regioselective and diastereoselective synthesis of highly functionalized and synthetically challenging bridged medium-sized polycyclic systems. Asymmetric total synthesis of nakafuran-8 was accomplished using this method as a key step. Quantum mechanical calculations demonstrate the mechanism of this transformation and the origins of its multiple selectivities. This reaction will inspire the design of the strategies to make complex bioactive molecules with bridged medium-sized polycyclic systems.

ChemInform Abstract: ASYMMETRIC TOTAL SYNTHESIS OF 11α-HYDROXYPROGESTERONE VIA A BIOMIMETIC POLYENE CYCLIZATION

1978 ◽  
Vol 9 (12) ◽  
Author(s):  
W. S. JOHNSON ◽  
R. S. BRINKMEYER ◽  
V. M. KAPOOR ◽  
T. M. YARNELL
Keyword(s):  
Total Synthesis ◽  
Asymmetric Total Synthesis

Asymmetric Total Synthesis of Norzoanthamine

2021 ◽  
Author(s):  
Zhengyuan Xin ◽  
Hui Wang ◽  
Haibing He ◽  
Xiaoli Zhao ◽  
Shuanhu Gao
Keyword(s):  
Total Synthesis ◽  
Asymmetric Total Synthesis

scholarly journals Asymmetric Total Synthesis of Hetiamacins A–F

ACS Omega ◽  
2021 ◽  
Vol 6 (12) ◽  
pp. 8239-8245
Author(s):  
Gang Wu ◽  
Ting Wang ◽  
Zhongke Jiang ◽  
Shaowei Liu ◽  
Chenghang Sun
Keyword(s):  
Total Synthesis ◽  
Asymmetric Total Synthesis

Asymmetric Total Synthesis and Determination of the Absolute Configuration of (+)-Srilankenyne via Sequence-Sensitive Halogenations Guided by Conformational Analysis

2021 ◽  
Vol 23 (4) ◽  
pp. 1321-1326
Author(s):  
Hongjun Jang ◽  
Soo Yeon Kwak ◽  
Dongjoo Lee ◽  
Juan V. Alegre-Requena ◽  
Hyoungsu Kim ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Conformational Analysis ◽  
Absolute Configuration ◽  
Asymmetric Total Synthesis ◽  
The Absolute

Asymmetric Total Synthesis of Amphirionin-2

2021 ◽  
Author(s):  
Dhiman Saha ◽  
Gour Hari Mandal ◽  
Rajib Kumar Goswami
Keyword(s):  
Total Synthesis ◽  
Asymmetric Total Synthesis
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