Second-generation total synthesis of aplyronine A featuring Ni/Cr-mediated coupling reactions

2017 ◽  
Vol 15 (1) ◽  
pp. 124-131 ◽  
Author(s):  
Ichiro Hayakawa ◽  
Keita Saito ◽  
Sachiko Matsumoto ◽  
Shinichi Kobayashi ◽  
Ayaka Taniguchi ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Second Generation ◽  
Coupling Reactions ◽  
Key Steps ◽  
Aplyronine A

Second-generation total synthesis of aplyronine A, a potent antitumor marine macrolide, was achieved using Ni/Cr-mediated coupling reactions as key steps.

scholarly journals Total syntheses of all tri-oxygenated 16-phytoprostane classes via a common precursor constructed by oxidative cyclization and alkyl–alkyl coupling reactions as the key steps

2017 ◽  
Vol 15 (44) ◽  
pp. 9408-9414 ◽  
Author(s):  
Jakub Smrček ◽  
Radek Pohl ◽  
Ullrich Jahn
Keyword(s):  
Total Synthesis ◽  
Oxidative Cyclization ◽  
Coupling Reactions ◽  
Total Syntheses ◽  
Common Precursor ◽  
Key Steps

A parallel total synthesis of 16-F1t-, 16-E1-phytoprostanes and a first synthesis of 16-D1t-phytoprostanes based on a common precursor are described.

scholarly journals First Stereoselective Total Synthesis of Ciryneol C

SynOpen ◽  
2019 ◽  
Vol 03 (02) ◽  
pp. 59-66
Author(s):  
Ambati Sharada ◽  
Lakshmi Srinivasa Rao Kundeti ◽  
Kallaganti V. S. Ramakrishna ◽  
Kommu Nagaiah
Keyword(s):  
Total Synthesis ◽  
Coupling Reactions ◽  
Asymmetric Total Synthesis ◽  
Acetylene Derivative ◽  
Wittig Olefination ◽  
Epoxide Opening ◽  
Key Steps

The acetylene derivative Ciryneol C was isolated from the roots of C. japonicum. The asymmetric total synthesis of Ciryneol C was achieved in seven steps, with Horner–Wittig olefination, regioselective epoxide opening, and Cadiot–Chodkiewicz coupling reactions being the key steps.

Applications of crotyldiisopinocampheylboranes in synthesis: a formal total synthesis of (+)-calyculin A

2001 ◽  
Vol 79 (11) ◽  
pp. 1562-1592 ◽  
Author(s):  
Oren P Anderson ◽  
Anthony GM Barrett ◽  
Jeremy J Edmunds ◽  
Shun-Ichiro Hachiya ◽  
James A Hendrix ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Marine Natural Product ◽  
Aldol Reactions ◽  
Calyculin A ◽  
Coupling Reactions ◽  
Stille Coupling ◽  
Palladium Catalyzed ◽  
Key Steps ◽  
Absolute Stereochemistry

The formal total synthesis of the marine metabolite (+)-calyculin A is reported. The key steps involve (i) the use of Brown allylboration chemistry to control the relative and absolute stereochemistry of homoallylic alcohol arrays, thus setting eight of the desired stereocenters; (ii) Stille coupling methodology in the construction of the cyano tetraene unit of the natural product; and (iii) a modified Cornforth–Meyers approach to the synthesis of the oxazole fragment.Key words: calyculin, marine natural product, phosphatase inhibitor, total synthesis, palladium catalyzed coupling reactions, allylboration reactions, aldol reactions, spiroketal, Cornforth–Meyers oxazole reaction.

Concise Total Synthesis of Curvulone B

Synlett ◽  
2020 ◽  
Author(s):  
Debendra K. Mohapatra ◽  
Shivalal Banoth ◽  
Utkal Mani Choudhury ◽  
Kanakaraju Marumudi ◽  
Ajit C. Kunwar
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Ring System ◽  
Bond Forming ◽  
Cross Metathesis ◽  
Bond Forming Reactions ◽  
Key Steps

AbstractA concise and convergent stereoselective synthesis of curvulone B is described. The synthesis utilized a tandem isomerization followed by C–O and C–C bond-forming reactions following Mukaiyama-type aldol conditions for the construction of the trans-2,6-disubstituted dihydropyran ring system as the key steps. Other important features of this synthesis are a cross-metathesis, epimerization, and Friedel–Crafts acylation.

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.

Aplyronine A, a Potent Antitumor Substance of Marine Origin, Aplyronines B and C, and Artificial Analogues:  Total Synthesis and Structure−Cytotoxicity Relationships

1996 ◽  
Vol 61 (16) ◽  
pp. 5326-5351 ◽  
Author(s):  
Hideo Kigoshi ◽  
Kiyotake Suenaga ◽  
Tsuyoshi Mutou ◽  
Takeshi Ishigaki ◽  
Toshiyuki Atsumi ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Marine Origin ◽  
Aplyronine A

Second-generation total synthesis of (−)-diversifolin

2010 ◽  
Vol 51 (14) ◽  
pp. 1876-1879 ◽  
Author(s):  
Kazuma Tsuboi ◽  
Tomoaki Nakamura ◽  
Takahiro Suzuki ◽  
Atsuo Nakazaki ◽  
Susumu Kobayashi
Keyword(s):  
Total Synthesis ◽  
Second Generation
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