Total Synthesis of (–)-HM-3 and (–)-HM-4 Utilizing a Palladium-Catalyzed Addition of an Arylboronic Acid to an Allenic Alcohol Followed by Eschenmoser–Claisen Rearrangement

Synlett ◽  
2014 ◽  
Vol 25 (08) ◽  
pp. 1160-1162 ◽  
Author(s):  
Masahiro Yoshida ◽  
Tomoyo Kasai ◽  
Tomotaka Mizuguchi ◽  
Kosuke Namba
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Arylboronic Acid ◽  
Palladium Catalyzed

Arylboronic Acid-Catalyzed C-Allylation of Unprotected Oximes

2019 ◽  
Author(s):  
Juha Siitonen ◽  
Padmanabha V. Kattamuri ◽  
Muhammed Yousufuddin ◽  
Laszlo Kurti
Keyword(s):  
Total Synthesis ◽  
Acid Catalysts ◽  
Mechanistic Studies ◽  
Arylboronic Acid ◽  
Synthetic Utility ◽  
Acid Catalyzed

Unprotected keto- and aldoximes are readily <i>C</i>-allylated with allyl diisopropyl boronate in the presence of arylboronic acid catalysts to yield highly-substituted <i>N</i>-alpha-secondary (2°) and tertiary (3°) hydroxylamines. The method’s synthetic utility is demonstrated with the total synthesis of the trace alkaloid <i>N</i>-methyl-euphococcine. Preliminary experimental and computational mechanistic studies point toward the formation of a boroxine as the active allylating species.<br>

Total Synthesis of Icaritin via Microwave-assistance Claisen Rearrangement

2014 ◽  
Vol 11 (9) ◽  
pp. 677-681 ◽  
Author(s):  
Van-Son Nguyen ◽  
Ling Shi ◽  
Yue Li ◽  
Qiu-An Wang
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Microwave Assistance

Total Syntheses of Enokipodins A and B Utilizing Palladium-Catalyzed Addition of An Arylboronic Acid to An Allene

2009 ◽  
Vol 11 (6) ◽  
pp. 1441-1443 ◽  
Author(s):  
Masahiro Yoshida ◽  
Yasunobu Shoji ◽  
Kozo Shishido
Keyword(s):  
Arylboronic Acid ◽  
Total Syntheses ◽  
Palladium Catalyzed
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