Total synthesis of heronapyrrole C

Ding, Xiao-Bo, Furkert, Daniel P., Capon, Robert J. and Brimble, Margaret A. (2014) Total synthesis of heronapyrrole C. Organic Letters, 16 2: 378-381. doi:10.1021/ol403246j


Author Ding, Xiao-Bo
Furkert, Daniel P.
Capon, Robert J.
Brimble, Margaret A.
Title Total synthesis of heronapyrrole C
Journal name Organic Letters   Check publisher's open access policy
ISSN 1523-7060
1523-7052
Publication date 2014-01-17
Year available 2013
Sub-type Article (original research)
DOI 10.1021/ol403246j
Volume 16
Issue 2
Start page 378
End page 381
Total pages 4
Place of publication Washington, DC, United States
Publisher American Chemical Society
Collection year 2015
Language eng
Formatted abstract
A flexible total synthesis of the 2-nitropyrrole-derived marine natural product, (+)-heronapyrrole C, is reported. The approach is based on regioselective access to key building blocks containing the rare 4-substituted 2-nitropyrrole motif. Sharpless asymmetric epoxidation and dihydroxylation and a Shi epoxidation were used to introduce the five stereogenic centers of the bis-THF-diol side chain. The N-benzoyloxymethyl (Boz) protecting group was crucial for functionalization of the 2- nitropyrrole moiety and enabling final deprotection under mild conditions.
Keyword Catalytic asymmetric epoxidation
Stereoselective-synthesis
Alkenes
Cascade
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ
Additional Notes Published online 18 December 2013

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2015 Collection
Institute for Molecular Bioscience - Publications
 
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