Enantioselective total synthesis of (+)-arborescidine C and related tetracyclic indole alkaloids using organocatalysis

2017 ◽  
Vol 15 (16) ◽  
pp. 3408-3412 ◽  
Author(s):  
Vishal M. Sheth ◽  
Bor-Cherng Hong ◽  
Gene-Hsiang Lee
Keyword(s):  
Total Synthesis ◽  
Indole Alkaloids ◽  
Enantioselective Synthesis ◽  
Cyclization Reaction ◽  
Enantioselective Total Synthesis

Enantioselective synthesis of (+)-arborescidine C was achieved by the key step of Pictet–Spengler cyclization reaction with a Jacobsen-type thiourea organocatalyst.

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.

Enantioselective total synthesis of (−)-kainic acid and (+)-acromelic acid C via Rh(i)-catalyzed asymmetric enyne cycloisomerization

2018 ◽  
Vol 54 (7) ◽  
pp. 727-730 ◽  
Author(s):  
Honghui Lei ◽  
Shan Xin ◽  
Yifan Qiu ◽  
Xumu Zhang
Keyword(s):  
Total Synthesis ◽  
Kainic Acid ◽  
Enantioselective Synthesis ◽  
Enantioselective Total Synthesis ◽  
Synthetic Strategy

A diversity-oriented synthetic strategy for the enantioselective synthesis of (−)-kainic acid and (+)-acromelic acid C is presented.

A Divergent Enantioselective Total Synthesis of Post‐Iboga Indole Alkaloids

2020 ◽  
Vol 132 (42) ◽  
pp. 18890-18899
Author(s):  
Jie Zhou ◽  
Dong‐Xing Tan ◽  
Fu‐She Han
Keyword(s):  
Total Synthesis ◽  
Indole Alkaloids ◽  
Enantioselective Total Synthesis

scholarly journals Towards stereochemical control: A short formal enantioselective total synthesis of pumiliotoxins 251D and 237A

2013 ◽  
Vol 9 ◽  
pp. 2358-2366 ◽  
Author(s):  
Jie Zhang ◽  
Hong-Kui Zhang ◽  
Pei-Qiang Huang
Keyword(s):  
Total Synthesis ◽  
Enantioselective Synthesis ◽  
Ring Closure ◽  
Enantioselective Total Synthesis ◽  
Stereochemical Control ◽  
Stereoselective Addition ◽  
Methylmagnesium Iodide

A concise enantioselective synthesis of the advanced intermediate 5 for the synthesis of pumiliotoxins (Gallagher’s intermediate) is described. The synthesis started from the regio- and trans-diastereoselective (dr = 98:2) reductive 3-butenylation of (R)-3-(tert-butyldimethylsilyloxy)glutarimide 14. After O-desilylation and Dess–Martin oxidation, the resulting keto-lactam 10 was subjected to a highly trans-stereoselective addition of the methylmagnesium iodide to give carbinol 11 as sole diastereomer. An efficient ring closure procedure consisting of ozonolysis and reductive dehydroxylation provided the indolizidine derivative 5, which completed the formal enantioselective total synthesis of pumiliotoxins 251D and 237A.

scholarly journals Enantioselective total synthesis of (R)-(−)-complanine

2012 ◽  
Vol 8 ◽  
pp. 1695-1699 ◽  
Author(s):  
Krystal A D Kamanos ◽  
Jonathan M Withey
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Causative Agent ◽  
Enantioselective Synthesis ◽  
Marine Natural Product ◽  
Enantioselective Total Synthesis ◽  
Efficient Access

A route is described for the enantioselective synthesis of (R)-(−)-complanine, a marine natural product isolated from Eurythoe complanata, and known to be a causative agent in inflammation. An organocatalytic, asymmetric oxyamination of a homoconjugated all-Z-dienal intermediate provides versatile and efficient access to the natural product.

scholarly journals Enantioselective total synthesis of (−)-colchicine, (+)-demecolcinone and metacolchicine: determination of the absolute configurations of the latter two alkaloids

2017 ◽  
Vol 8 (7) ◽  
pp. 4961-4966 ◽  
Author(s):  
Bo Chen ◽  
Xin Liu ◽  
Ya-Jian Hu ◽  
Dong-Mei Zhang ◽  
Lijuan Deng ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Enantioselective Synthesis ◽  
Enantioselective Total Synthesis ◽  
The Absolute

A highly concise, enantioselective synthesis of (−)-colchicine, the first syntheses of (+)-demecolcinone and metacolchicine, was reported.

Enantioselective total synthesis and biological evaluation of (−)-solanacol

2018 ◽  
Vol 16 (30) ◽  
pp. 5500-5507 ◽  
Author(s):  
L. J. Bromhead ◽  
A. R. Norman ◽  
K. C. Snowden ◽  
B. J. Janssen ◽  
C. S. P. McErlean
Keyword(s):  
Total Synthesis ◽  
Phenyl Ring ◽  
Biological Evaluation ◽  
Enantioselective Synthesis ◽  
Enantioselective Total Synthesis ◽  
Synthesis And Biological Evaluation

An enantioselective synthesis of the phenyl ring-containing strioglactone, (−)-solanocol, is 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.

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