Total Synthesis of (−)-Hippodamine by Stereocontrolled Construction of Azaphenalene Skeleton Based on Extended One-Pot Asymmetric Azaelectrocyclization

The first asymmetric total synthesis of (−)-hippodamine has been accomplished via the concise construction of its azaphenalene core, which is featured by the 2,4,6-chiral piperidine synthesis based on one-pot asymmetric azaelectrocyclization in the partially activated substituent system and the subs...

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Bibliographic Details
Published inOrganic letters Vol. 15; no. 11; pp. 2758 - 2761
Main Authors Fujita, Shintaro, Sakaguchi, Taku, Kobayashi, Toyoharu, Tsuchikawa, Hiroshi, Katsumura, Shigeo
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.06.2013
Amer Chemical Soc
Subjects
Aza Compounds - chemical synthesis
Aza Compounds - chemistry
Chemistry
Chemistry, Organic
Cyclization
Molecular Structure
Physical Sciences
Piperidines - chemistry
Quinazolines - chemical synthesis
Quinazolines - chemistry
Science & Technology
Stereoisomerism
PRECOCCINELLINE
COCCINELLINE
MYRRHINE
FORMAL SYNTHESIS
6-PI-AZAELECTROCYCLIZATION
CHIRAL PIPERIDINES
HIPPODAMINE
7-ALKYL SUBSTITUTED CIS-1-AMINO-2-INDANOLS
(-)-DENDROPRIMINE
ALKALOIDS
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Summary:The first asymmetric total synthesis of (−)-hippodamine has been accomplished via the concise construction of its azaphenalene core, which is featured by the 2,4,6-chiral piperidine synthesis based on one-pot asymmetric azaelectrocyclization in the partially activated substituent system and the subsequent intramolecular Mannich reaction.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol4010917