NDLI: Stereospecific Synthesis of Eight-Membered Polyhydroxy Carbocycles via TIBAL-Promoted Claisen Rearrangement

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Stereospecific Synthesis of Eight-Membered Polyhydroxy Carbocycles via TIBAL-Promoted Claisen Rearrangement

Content Provider	Scilit
Author	Zhang, Liang Ren Han, Tianxiang Liu, Yi Yang, Zhenjun Zhang, Lihe
Copyright Year	2008
Description	The stereoselective synthesis of novel eight-membered polyhydroxy carbocycles was achieved from d-glucose via mercuriocyclization and triisobutylaluminum (TIBAL)-promoted Claisen rearrangement. Along with rearrangement, TIBAL also promoted debenzylation and cycloaddition, and a 3,9-dioxa-bicyclo[3.3.1]nonane derivative was formed. The stereoselectivity of mercuriocyclization was attributed to the interaction between mecurio and vinyl moities, and this interaction also assisted the mercurio derivative to exist in an abnormal conformation. The configuration and/or conformation of intermediates and products were identified by NMR spectral analyses.
Related Links	http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2008-1077965.pdf
Ending Page	1988
Page Count	4
Starting Page	1985
ISSN	09365214
e-ISSN	14372096
DOI	10.1055/s-2008-1077965
Journal	Synlett
Issue Number	13
Volume Number	2008
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2008-07-15
Access Restriction	Open
Subject Keyword	Organic Chemistry Mercuriocyclization Claisen Rearrangement
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry

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