Stereoselective Halogenation in Natural Product Synthesis

At last count, nearly 5000 halogenated natural products have been discovered. In approximately half of these compounds, the carbon atom to which the halogen is bound is sp3‐hybridized; therefore, there are an enormous number of natural products for which stereocontrolled halogenation must be a criti...

Celý popis

Uložené v:
Podrobná bibliografia
Vydané v:Angewandte Chemie International Edition Ročník 55; číslo 14; s. 4396 - 4434
Hlavní autori: Chung, Won-jin, Vanderwal, Christopher D.
Médium: Journal Article
Jazyk:English
Vydavateľské údaje: Germany Blackwell Publishing Ltd 24.03.2016
Wiley Subscription Services, Inc
Vydanie:International ed. in English
Predmet:
asymmetric synthesis
Biological Products - chemical synthesis
Halogenation
Natural products
stereochemistry
Stereoisomerism
total synthesis
stereochemistry
natural products
halogenation
asymmetric synthesis
total synthesis
ISSN:1433-7851, 1521-3773
On-line prístup:Získať plný text
Tagy: Pridať tag
Žiadne tagy, Buďte prvý, kto otaguje tento záznam!
Popis
Shrnutí:At last count, nearly 5000 halogenated natural products have been discovered. In approximately half of these compounds, the carbon atom to which the halogen is bound is sp3‐hybridized; therefore, there are an enormous number of natural products for which stereocontrolled halogenation must be a critical component of any synthesis strategy. In this Review, we critically discuss the methods and strategies used for stereoselective introduction of halogen atoms in the context of natural product synthesis. Using the successes of the past, we also attempt to identify gaps in our synthesis technology that would aid the synthesis of halogenated natural products, as well as existing methods that have not yet seen application in complex molecule synthesis. The chemistry described herein demonstrates yet again how natural products continue to provide the inspiration for critical advances in chemical synthesis. With thousands of natural products containing halogen‐bearing stereogenic centers, a wealth of methods have been developed for their stereocontrolled introduction in the context of total synthesis. This Review highlights the creative ways in which organic chemists have dealt with the challenges of stereochemically rich, halogenated natural products.
Bibliografia:ark:/67375/WNG-2J4CJ3NJ-6
National Institutes of Health - No. GM-086483
istex:F08F5B727791B00381AA4A5FBA3C87F41B19AE65
ArticleID:ANIE201506388
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
ObjectType-Feature-3
content type line 23
ObjectType-Review-2
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201506388