NDLI: Total Synthesis of (–)-Stemoamide by Sequential Overman/Claisen Rearrangement

Content Provider	Scilit
Author	Sato, Takaaki Chida, Noritaka Nakayama, Yasuaki Maeda, Yuichiro Hama, Naoto
Copyright Year	2016
Description	The enantioselective total synthesis of (–)-stemoamide using Overman/Claisen rearrangement of an allylic 1,2-diol is reported. The enantiopure allylic 1,2-diol was efficiently prepared from naturally occurring dimethyl tartrate. The chirality transfer reactions through two consecutive [3,3]-sigmatropic rearrangements proceeded with complete diastereoselectivity in a one-pot process.
Related Links	http://pdfs.semanticscholar.org/cd67/c81a9e451fc6266de171605821dade75e9e9.pdf http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0035-1561948.pdf
Ending Page	1654
Page Count	8
Starting Page	1647
ISSN	00397881
e-ISSN	1437210X
DOI	10.1055/s-0035-1561948
Journal	Synthesis
Issue Number	11
Volume Number	48
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2016-03-22
Access Restriction	Open
Subject Keyword	Journal: Synthesis Organic Chemistry Allylic Compound Sigmatropic Rearrangement Total Synthesis
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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Total Synthesis of (–)-Stemoamide by Sequential Overman/Claisen Rearrangement