Oxidative Entry into the Illicium Sesquiterpenes: Enantiospecific Synthesis of (+)-Pseudoanisatin

Illicium sesquiterpenes have been the subject of numerous synthetic efforts due to their ornate and highly oxidized structures as well as significant biological activities. Herein we report the first chemical synthesis of (+)-pseudoanisatin from the abundant feedstock chemical cedrol (∼$50 USD/kg) i...

Full description

Saved in:
Bibliographic Details
Published inJournal of the American Chemical Society Vol. 138; no. 51; pp. 16616 - 16619
Main Authors Hung, Kevin, Condakes, Matthew L, Morikawa, Takahiro, Maimone, Thomas J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 28.12.2016
Amer Chemical Soc
Subjects
bioactive properties
cedrol
Chemistry
Chemistry, Multidisciplinary
feedstocks
Illicium
Physical Sciences
Science & Technology
synthesis
ALCOHOLS
JIADIFENOLIDE
NATURAL-PRODUCTS
(+/-)-MERRILACTONE-A
NEUROTROPHIC ACTIVITY
C-H OXIDATION
(-)-JIADIFENOLIDE
ENANTIOSELECTIVE TOTAL-SYNTHESIS
SECO-PREZIZAANE
DIRECTED DIHYDROXYLATION
Online AccessGet full text

Cover

More Information
Summary:Illicium sesquiterpenes have been the subject of numerous synthetic efforts due to their ornate and highly oxidized structures as well as significant biological activities. Herein we report the first chemical synthesis of (+)-pseudoanisatin from the abundant feedstock chemical cedrol (∼$50 USD/kg) in 12 steps using extensive site-selective C­(sp3)–H bond functionalization. Significantly, this work represents a novel oxidative strategic template for future approaches to these natural products and their analogs.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
Author Contributions: These authors contributed equally.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.6b11739