scholarly journals Construction of the Pentacyclic Core and Formal Total Synthesis of (rac )-Renieramycin T

ChemistryOpen ◽  
2018 ◽  
Vol 7 (10) ◽  
pp. 764-771 ◽  
Author(s):  
Shinya Kimura ◽  
Naoki Saito
Keyword(s):  
Total Synthesis ◽  
Pentacyclic Core

scholarly journals Synthesis of (–)-Kopsifoline A and (+)-Kopsifoline E

2021 ◽  
Author(s):  
In-Soo Myeong ◽  
Nadide Hazal Avci ◽  
Mohammad Movassaghi
Keyword(s):  
Total Synthesis ◽  
Bond Formation ◽  
Mitsunobu Reaction ◽  
Reaction Conditions ◽  
Synthetic Strategy ◽  
F Ring ◽  
Pentacyclic Core

We report the first total synthesis of (–)-kopsifoline A and (+)-kopsifoline E. Our synthetic strategy features a biogenetically inspired regioselective C17-functionalization of a versatile intermediate containing the pentacyclic core of aspidosperma alkaloids. While this advance intermediate provides (–)-kopsifoline D via C3–C21 bond formation, regioselective C17-boronation of its indoline substructure prior to introduction of the F-ring enables access to (–)-kopsifoline A and (+)-kopsifoline E. The vinylogous urethane substructure of the key intermediate was critical in C17-boronation over a competing C7-boronation in related indole derived substrates. After oxidation of the C17–B bond to introduce the C17-ether, the C3–C21 bond of the targets is secured under the Mitsunobu reaction conditions with the vinylogous urethane as the nucleophilic component.

Total synthesis study of rauvomines A and B: construction of the pentacyclic core structure

2020 ◽  
Vol 7 (13) ◽  
pp. 1685-1689
Author(s):  
Binglu Wu ◽  
Zhi-Jiang Jiang ◽  
Jianbo Tang ◽  
Zhanghua Gao ◽  
Hongze Liang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Core Structure ◽  
Mukaiyama Aldol Reaction ◽  
New Strategy ◽  
Mukaiyama Aldol ◽  
Pentacyclic Core

The fifth ring of rauvomines can be annulated via a Mukaiyama-Aldol reaction as a new strategy for sarpagine scaffold construction.

scholarly journals Catalytic stereoselective total synthesis of a spiro-oxindole alkaloid and the pentacyclic core of tryptoquivalines

2018 ◽  
Vol 54 (91) ◽  
pp. 12860-12862 ◽  
Author(s):  
Tao Wei ◽  
Darren J. Dixon
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Pentacyclic Core

An expedient route to the pentacyclic core of the tryptoquivaline alkaloids and the total synthesis of natural product (+)-3′-(4-oxoquinazolin-3-yl)spiro[1H-indole-3,5′-oxolane]-2,2′-dione (1) have been achieved.

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