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Total Synthesis of Plakortide E and Biomimetic Synthesis of Plakortone B.
MedLine Citation:
PMID:  21491517     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
The total synthesis of plakortide E (1 a) is reported. A novel palladium-catalyzed approach towards 1,2-dioxolanes as well as an alternative substrate-controlled route leading exclusively to cis-highly substituted 1,2-dioxolanes have been developed. A lipase-catalyzed kinetic resolution was employed to provide optically pure 1,2-dioxolane central cores. Coupling of the central cores and side chains was achieved by a modified Negishi reaction. All four isomeric structures of plakortide E methyl ester, namely, 26 a-d were synthesized. One of the structures, 26 d, was shown to be identical with the natural plakortide E methyl ester on the basis of (1) H, (13) C NMR spectra and specific rotation comparisons. With the plakortide E methyl ester (4S,6R,10R)-(-)-cis-26 d and its other three isomers in hand, we successfully converted them into (3S,4S,6R,10R)-plakortone B (2 a), and its isomers ent-2 a, 2 b and ent-2 b via an intramolecular oxa-Michael addition/lactonization cascade reaction. Finally, saponification converted 1,2-dioxolane 26 d into plakortide E (1 a) whose absolute configuration (4S,6R,10R) was confirmed by comparison of spectral and physical data with those reported.
Authors:
Xiao-Yu Sun; Xiang-Yin Tian; Zhen-Wu Li; Xiao-Shui Peng; Henry N C Wong
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-4-13
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  -     ISSN:  1521-3765     ISO Abbreviation:  -     Publication Date:  2011 Apr 
Date Detail:
Created Date:  2011-4-14     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Affiliation:
Department of Chemistry, Centre of Novel Functional Molecules, Institute of Chinese Medicine and Institute of Molecular Technology for Drug Discovery and Synthesis, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR (P.R. China), Fax: (+852) 26096329.
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