Total Synthesis of Lapidilectine B Enabled by Manganese(III)-Mediated Oxidative Cyclization of Indoles

2018 ◽  
Vol 24 (25) ◽  
pp. 6547-6550 ◽  
Author(s):  
Yang Gao ◽  
Mengyang Fan ◽  
Qixiang Geng ◽  
Dawei Ma
Keyword(s):  
Total Synthesis ◽  
Oxidative Cyclization ◽  
Lapidilectine B

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 Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for the Enantioselective Total Synthesis of Mavacuran Alkaloids

2019 ◽  
Author(s):  
Maxime Jarret ◽  
Victor Turpin ◽  
Aurélien Tap ◽  
Jean-Francois Gallard ◽  
Cyrille Kouklovsky ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Indole Alkaloids ◽  
Oxidative Cyclization ◽  
Total Syntheses ◽  
Enantioselective Total Synthesis ◽  
Biosynthetic Precursor ◽  
Monoterpene Indole Alkaloids ◽  
Coupling Approach

We report the enantioselective total syntheses of mavacurans alkaloids, (+)-taberdivarine H, (+)-16-hydoxymethyl-pleiocarpamine, (+)-16-epi-pleiocarpamine, and their postulated biosynthetic precursor 16-formyl-pleiocarpamine. This family of monoterpene indole alkaloids is a target of choice since some of its members are subunits of intricate bisindole alkaloids such as bipleiophylline. Inspired by the biosynthetic hypothesis, we explored an oxidative coupling approach from the geissoschizine framework to form the N1-C16 bond. Quaternization of the aliphatic nitrogen was key to achieve the oxidative coupling induced by KHMDS/I<sub>2 </sub>since<sub> </sub>it hides the nucleophilicity of the aliphatic nitrogen and locks the required cis conformation.

scholarly journals First Total Synthesis and Investigation of the X-ray Crystal Structure of the Pyrano[3,2-a]carbazole Alkaloid Clausenalansine A

Synthesis ◽  
2020 ◽  
Vol 53 (02) ◽  
pp. 359-364
Author(s):  
Hans-Joachim Knölker ◽  
Valerie Lösle ◽  
Olga Kataeva
Keyword(s):  
Crystal Structure ◽  
Total Synthesis ◽  
Lewis Acid ◽  
Oxidative Cyclization ◽  
Formyl Group ◽  
Pyran Ring ◽  
X Ray ◽  
Synthetic Strategy

AbstractWe describe the first total synthesis of the recently discovered pyrano[3,2-a]carbazole alkaloid clausenalansine A. The synthetic strategy for the construction of this formylpyrano[3,2-a]carbazole is based on a sequence of Buchwald–Hartwig coupling, palladium(II)-catalyzed oxidative cyclization, Lewis acid promoted annulation of the pyran ring, and chemoselective oxidation of a methyl to a formyl group.

scholarly journals Enantioselective Total Synthesis of Cymoside through a Bioinspired Oxidative Cyclization of a Strictosidine Derivative

2019 ◽  
Vol 132 (4) ◽  
pp. 1543-1547 ◽  
Author(s):  
Yingchao Dou ◽  
Cyrille Kouklovsky ◽  
Vincent Gandon ◽  
Guillaume Vincent
Keyword(s):  
Total Synthesis ◽  
Oxidative Cyclization ◽  
Enantioselective Total Synthesis

ChemInform Abstract: Total Synthesis of the Kopsia lapidilecta Alkaloid (.+-.)-Lapidilectine B.

ChemInform ◽  
2010 ◽  
Vol 32 (43) ◽  
pp. no-no
Author(s):  
William H. Pearson ◽  
Yuan Mi ◽  
Ill Young Lee ◽  
Patrick Stoy
Keyword(s):  
Total Synthesis ◽  
Lapidilectine B

Total synthesis of demethylwedelolactone and wedelolactone by Cu-mediated/Pd(0)-catalysis and oxidative-cyclization

Tetrahedron ◽  
2008 ◽  
Vol 64 (17) ◽  
pp. 3661-3666 ◽  
Author(s):  
Chia-Fu Chang ◽  
Ling-Yi Yang ◽  
Shiao-Wei Chang ◽  
Yu-Ting Fang ◽  
Yean-Jang Lee
Keyword(s):  
Total Synthesis ◽  
Oxidative Cyclization

scholarly journals Total synthesis of ochnaflavone

2013 ◽  
Vol 9 ◽  
pp. 1346-1351 ◽  
Author(s):  
Monica M Ndoile ◽  
Fanie R van Heerden
Keyword(s):  
Total Synthesis ◽  
Oxidative Cyclization ◽  
Experimental Conditions ◽  
Total Syntheses ◽  
Diaryl Ether ◽  
Key Steps

The first total syntheses of ochnaflavone, an asymmetric biflavone consisting of apigenin and luteolin moieties, and the permethyl ether of 2,3,2'',3''-tetrahydroochnaflavone have been achieved. The key steps in the synthesis of ochnaflavone were the formation of a diaryl ether and ring cyclization of an ether-linked dimeric chalcone to assemble the two flavone nuclei. Optimal experimental conditions for the oxidative cyclization to form ochnaflavone were established.

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