A Formal Synthesis of (–)-Kainic Acid by Means of SmI2-Mediated Radical Cyclization

Heterocycles ◽  
2018 ◽  
Vol 96 (5) ◽  
pp. 882 ◽  
Author(s):  
Kazunori Takahashi ◽  
Takumi Ito ◽  
Wataru Yamada ◽  
Masayoshi Tsubuki ◽  
Toshio Honda
Keyword(s):  
Kainic Acid ◽  
Radical Cyclization ◽  
Formal Synthesis

scholarly journals Expedient Access to Enantiopure Cyclopentanic Natural Products: Total Synthesis of (-)-Cyclonerodiol

2015 ◽  
Vol 10 (1) ◽  
pp. 1934578X1501000
Author(s):  
Carmen Pérez Morales ◽  
M. Mar Herrador ◽  
José F. Quílez del Moral ◽  
Alejandro F. Barrero
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Radical Cyclization ◽  
Formal Synthesis ◽  
Common Precursor ◽  
Enantiospecific Synthesis ◽  
Optically Pure

Following the principles of collective total synthesis, a number of natural products sharing an optically pure, multifunctional, cyclopentanic core were synthesized from a common precursor: plinol A (1). This intermediate was efficiently obtained in only four steps from (-)-linalool (2) using as the key step a Ti(III)-mediated diastereoselective radical cyclization. The feasibility of this approach was confirmed with the expedient enantiospecific synthesis of cyclonerodiol (3), and the formal synthesis of chocol G (4) and piperitone (5).

ChemInform Abstract: A New Enantioselective Route to Kainoids: Application to the Formal Synthesis of (-)-α-Kainic Acid (I).

ChemInform ◽  
2010 ◽  
Vol 22 (34) ◽  
pp. no-no
Author(s):  
A. BARCO ◽  
S. BENETTI ◽  
G. P. POLLINI ◽  
G. SPALLUTO ◽  
V. ZANIRATO
Keyword(s):  
Kainic Acid ◽  
Formal Synthesis

ChemInform Abstract: Stereoselective Formal Synthesis of (+)-Allokainic Acid via Thiol-Mediated Acyl Radical Cyclization.

ChemInform ◽  
2011 ◽  
Vol 42 (13) ◽  
pp. no-no
Author(s):  
Ken-ichi Yamada ◽  
Tomohiro Sato ◽  
Masaki Hosoi ◽  
Yasutomo Yamamoto ◽  
Kiyoshi Tomioka
Keyword(s):  
Radical Cyclization ◽  
Acyl Radical ◽  
Formal Synthesis

Formal Synthesis of FPA, a Kainoid Amino Acid, via Ketyl Radical Cyclization

Heterocycles ◽  
2002 ◽  
Vol 56 (1-2) ◽  
pp. 105 ◽  
Author(s):  
Haruhisa Shirahama ◽  
Mitsuru Kamabe ◽  
Takayuki Miyazaki ◽  
Kimiko Hashimoto
Keyword(s):  
Amino Acid ◽  
Radical Cyclization ◽  
Ketyl Radical ◽  
Formal Synthesis

scholarly journals Short Enantioselective Formal Synthesis of (–)-Platencin

Synthesis ◽  
2018 ◽  
Vol 50 (22) ◽  
pp. 4359-4368 ◽  
Author(s):  
Brian Stoltz ◽  
Christian Defieber ◽  
Justin Mohr ◽  
Gennadii Grabovyi
Keyword(s):  
Natural Product ◽  
Radical Cyclization ◽  
Formal Synthesis ◽  
Aldol Cyclization ◽  
Key Steps

A short enantioselective formal synthesis of the antibiotic natural product platencin is reported. Key steps in the synthesis include enantioselective decarboxylation alkylation, aldehyde/olefin radical cyclization, and regioselective aldol cyclization.

ChemInform Abstract: Radical Cyclization of β-Alkoxyacrylates: A Formal Synthesis of (-)-Kumausallene.

ChemInform ◽  
2010 ◽  
Vol 29 (15) ◽  
pp. no-no
Author(s):  
E. LEE ◽  
S.-K. YOO ◽  
H. CHOO ◽  
H. Y. SONG
Keyword(s):  
Radical Cyclization ◽  
Formal Synthesis
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