Short synthesis of phenylpropanoid glycoside grayanoside-A and analogues

A Short Synthesis of (+)-Brefeldin C via Enantioselective Radical Hydroalkynylation

10.26434/chemrxiv.8397731.v1 ◽

2019 ◽

Author(s):

Lars Gnägi ◽

Severin Vital Martz ◽

Daniel Meyer ◽

Robin Marc Schärer ◽

Philippe Renaud

Keyword(s):

Total Synthesis ◽

Natural Product ◽

Oxidation State ◽

Single Step ◽

Radical Process ◽

Target Molecule ◽

Short Synthesis ◽

The One

<div><div><div><div><p>A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows to achieve a high trans diastereoselectivity during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis require six product purifications and it provides (+)-brefeldin C in 18% overall yield.</p></div></div></div></div>

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A new phenylpropanoid glycoside from the fruits of Illicium simonsii

Chinese Journal of Natural Medicines ◽

10.3724/sp.j.1009.2012.00020 ◽

2012 ◽

Vol 10 (1) ◽

pp. 20-23 ◽

Cited By ~ 4

Author(s):

Dan-Dan WEI ◽

Jun-Song WANG ◽

Yao ZHANG ◽

Ling-Yi KONG

Keyword(s):

Phenylpropanoid Glycoside

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A Short Synthesis of the Plant Alkaloid 4-Methyl-2,6-naphthyridine

Letters in Organic Chemistry ◽

10.2174/1570178616666181116110647 ◽

2019 ◽

Vol 16 (12) ◽

pp. 931-934 ◽

Cited By ~ 2

Author(s):

Alexandra Kamlah ◽

Franz Bracher

Keyword(s):

Pyridine Ring ◽

Cross Coupling ◽

Antirrhinum Majus ◽

New Synthesis ◽

Short Synthesis ◽

Regioselective Oxidation ◽

Key Steps

: A new synthesis of the 2,6-naphthyridine alkaloid 4-methyl-2,6-naphthyridine from Antirrhinum majus has been developed. Key steps are a regioselective oxidation of 3-bromo-4,5- dimethylpyridine to the corresponding 4-formyl derivative, and the annulation of the second pyridine ring by Suzuki-Miyaura cross-coupling using (E)-2-ethoxyvinylboronic acid pinacol ester as a masked acetaldehyde equivalent. This protocol gives the alkaloid in four steps starting from commercially available 3,4-dimethylpyridine in 15% overall yield. This annulation protocol should be useful for the synthesis of other condensed pyridines as well.

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