Total Synthesis of Macaranin B

2021 ◽  
Author(s):  
Shintaro Matsumoto ◽  
Akio Aoyama ◽  
Shinnosuke Wakamori ◽  
Hidetoshi Yamada
Keyword(s):  
Total Synthesis ◽  
Michael Addition ◽  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Oxidative Coupling Reaction ◽  
Naturally Occurring ◽  
Key Steps

Abstract This study describes the total synthesis of macaranin B, a naturally occurring ellagitannin containing 1-O-galloyl and 3,6-O-macaranoyl groups in an axial-rich D-glucose. The Key steps of the synthesis include an oxidative coupling reaction of galloyl groups with 1,2,4-orthoacetylglucose moiety and oxa-Michael addition/elimination using an orthoquinone monoketal. This facilitates the construction of the macaranoyl group and the first total synthesis of macaranin B.

scholarly journals Total Synthesis of Surinamensinols A and B

SynOpen ◽  
2020 ◽  
Vol 04 (04) ◽  
pp. 84-88
Author(s):  
Ahmed Al-Harrasi ◽  
Satya Kumar Avula ◽  
Biswanath Das ◽  
Rene Csuk ◽  
Ahmed Al-Rawahi
Keyword(s):  
Total Synthesis ◽  
Allyl Alcohol ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Ethyl Lactate ◽  
Naturally Occurring ◽  
Cross Coupling Reaction ◽  
Synthetic Sequence ◽  
Key Steps ◽  
Single Approach

AbstractAn efficient total synthesis of the naturally occurring anti-inflammatory and antitumour 8-O-4′-neolignans, surinamensinols A and B, has been accomplished from commercially available allyl alcohol and (S)-ethyl lactate. The synthetic sequence involves a palladium-catalysed Suzuki–Miyaura cross-coupling reaction followed by a chiral Mitsunobu­ reaction as the key steps. This is the first report of the simultaneous stereoselective total synthesis of surinamensinols A and B through a single approach involving only six steps.

An Unprecedented Cyano-Induced Sodium Nitrite-Catalyzed C(sp3)-H and C(sp2)-H Coupling Reaction

2018 ◽  
Vol 15 (7) ◽  
pp. 989-994 ◽  
Author(s):  
Ling Li ◽  
Bo Su ◽  
Yuxiu Liu ◽  
Qingmin Wang
Keyword(s):  
Sodium Nitrite ◽  
Oxidative Coupling ◽  
High Resolution Mass Spectrometry ◽  
Coupling Reaction ◽  
13C Nmr Spectroscopy ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
1H And 13C Nmr ◽  
Oxidative Coupling Reaction ◽  
Oxidative Coupling Reactions

Aim and Objective: During the investigation of sodium nitrite-catalyzed oxidative coupling reaction of aryls, an unprecedented C(sp2)-H and C(sp3)-H coupling of substituted 2-aryl acetonitrile was found. Materials and Methods: The structure of the coupled product was confirmed by 1H and 13C NMR spectroscopy and high-resolution mass spectrometry (HRMS), and comparison of its derivatives with known compounds. The effects of methoxy group in the benzene ring on the reaction were evaluated. Results: The optimized reaction conditions are summarized as follows: CF3SO3H/substrate = 1.5 equiv., NaNO2/substrate = 0.3 equiv., CH3CN as solvent. 2-(4-Methoxyphenyl)acetonitrile and 2-(3,4,5- trimethoxyphenyl)acetonitrile could also generate C(sp2)-H and C(sp3)-H coupling. The coupling reaction occurred as a typical radial mechanism. Conclusion: An unprecedented cyano-induced, NaNO2-catalyzed oxidative C(sp3)-H and C(sp2)-H coupling was reported. The reaction proceeded under very mild conditions, using O2 in the air as terminal oxidant. The unique oxidative manner might provide more inspiration for the development of intriguing oxidative coupling reactions.

A Three Component Iodine-Catalyzed Oxidative Coupling Reaction: A Heterodifunction of 3-Methylindole

2021 ◽  
Author(s):  
Wei Zhang ◽  
Shiqun Xiang ◽  
Weibin Fan ◽  
Jiang Jin ◽  
Yinghua Li ◽  
...  
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Peroxy Radicals ◽  
Metal Free ◽  
Tert Butyl ◽  
Oxidative Coupling Reaction

A metal-free synthesis of heterodifunctional indole derivaties is developed through TBHP/KI-mediated oxidative coupling. The reaction constructs C-O and C-C bonds in succession with the help of tert-butyl peroxy radicals generated...

Direct visualization of photo-induced disulfides through oxidative coupling of para-aminothiophenol

2021 ◽  
Author(s):  
Wei He ◽  
Chang Xia ◽  
Peng Fei Gao ◽  
Jun Zhou ◽  
Yuan Fang Li ◽  
...  
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Chemical Transformations ◽  
Direct Visualization ◽  
Oxidative Coupling Reaction ◽  
Visible Irradiation

Chemical transformations under visible irradiation are interesting in green preparation. Herein, photo-oxidative coupling reaction of para-aminothiophenol(p-ATP) dimerizing to 4-aminophenyl disulfide(APDS) rather than 4,4′-dimercaptoazobenzene(DMAB) was achieved in water by visible irradiation,...

Synthesis of blue light emitting copolymers by oxidative coupling reaction

2003 ◽  
Vol 135-136 ◽  
pp. 201-202 ◽  
Author(s):  
Yingfeng Yu ◽  
Minghai Wang ◽  
Wei Huang ◽  
Shanjun Li
Keyword(s):  
Blue Light ◽  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Light Emitting ◽  
Oxidative Coupling Reaction

A New Entry to Carbocyclic Nucleosides: Oxidative Coupling Reaction of Cycloalkenylsilanes with a Nucleobase Mediated by Hypervalent Iodine Reagent

2008 ◽  
Vol 10 (16) ◽  
pp. 3449-3452 ◽  
Author(s):  
Yuichi Yoshimura ◽  
Masatoshi Ohta ◽  
Tatsushi Imahori ◽  
Tomozumi Imamichi ◽  
Hiroki Takahata
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Hypervalent Iodine ◽  
Carbocyclic Nucleosides ◽  
Oxidative Coupling Reaction ◽  
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