Facile access to some chiral building blocks. Synthesis of verbalactone and exophilin A

d-Glucono-1,5-lactone, an inexpensive carbohydrate, was elaborated into chiral building blocks readily applicable in synthesis via practical routes without involving any expensive reagents or tedious operations. Application of such chiral building blocks in total synthesis is then exemplified throug...

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Bibliographic Details
Published in:Tetrahedron 2009-01, Vol.65 (1), p.289-299
Main Authors: Wu, Jian-Zhong, Gao, Jian, Ren, Guo-Bao, Zhen, Zhi-Bin, Zhang, Yihua, Wu, Yikang
Format: Article
Language:English
Subjects:
Carbohydrates
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Chiron
Enantioselective synthesis
Epoxides
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Natural products
Organic chemistry
Preparations and properties
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Description
Summary:d-Glucono-1,5-lactone, an inexpensive carbohydrate, was elaborated into chiral building blocks readily applicable in synthesis via practical routes without involving any expensive reagents or tedious operations. Application of such chiral building blocks in total synthesis is then exemplified through construction of verbalactone and exophilin A. The latter compound has not been synthesized to date. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.10.050