Acid-Catalyzed Ring-Opening Cyclization of Spirocyclopropanes for the Construction of a 2-Arylbenzofuran Skeleton: Total Synthesis of Cuspidan B

Synthesis ◽  
2016 ◽  
Vol 48 (12) ◽  
pp. 1892-1901 ◽  
Author(s):  
Hisanori Nambu ◽  
Takayuki Yakura ◽  
Naoki Ono
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Acid 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>

First Total Synthesis of a Fluorinated Calystegin

2010 ◽  
Vol 65 (4) ◽  
pp. 445-451 ◽  
Author(s):  
René Csuk ◽  
Erik Prell ◽  
Stefan Reißmann ◽  
Claudia Korb
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Competitive Inhibitor ◽  
Ring Closure ◽  
Target Compound ◽  
Metathesis Reaction ◽  
Grubbs Catalyst ◽  
Ring Opening Reaction ◽  
Ultrasound Assisted ◽  
Key Steps

A straightforward chiral pool synthesis for the first fluorinated calystegin is described. Key steps of this synthesis include an ultrasound-assisted Zn-mediated tandem ring opening reaction followed by a Grubbs’ catalyst-mediated ring closure metathesis reaction. The target compound is a selective and competitive inhibitor for a β -glycosidase.

Total Synthesis of Resolvin T4

Synlett ◽  
2021 ◽  
Author(s):  
Narihito Ogawa ◽  
Kohei Arai ◽  
Yuichi Kobayashi
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Ring Opening Reaction ◽  
Propargylic Alcohol ◽  
Chiral Centers ◽  
Wittig Reactions

AbstractA total synthesis of resolvin T4 was achieved by connecting three intermediates by Wittig reactions. The enal in the C1–C10 part was constructed through reduction of a propargylic alcohol with Red-Al followed by oxidation. The enal moiety in the C11–C16 part was synthesized by a ring-opening reaction of a silyl epoxide followed by a Peterson elimination. The chiral centers at C7 and C13 were constructed by ruthenium-catalyzed asymmetric transfer hydrogenation.

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