Novel and Efficient Syntheses of Four Useful Shikimate- derived Epoxy Chiral Building Blocks via Cyclic Sulfite Intermediates

All of the four stereoisomers of methyl 4,5-epoxy-3-hydroxy-cyclohex-l-ene-carboxylate (la--ld) are useful chiral building blocks. Novel and efficient syntheses of these four epoxy chiral building blocks from naturally abun- dant (--)-shikimic acid (2) via cyclic sulfite intermediates are described...

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Veröffentlicht in:Chinese journal of chemistry 2012-12, Vol.30 (12), p.2759-2766
Hauptverfasser: Quan, Na, Nie, Liangdeng, Shi, Xiaoxin, Zhu, Ruiheng, Lü, Xia
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Sprache:eng
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Zusammenfassung:All of the four stereoisomers of methyl 4,5-epoxy-3-hydroxy-cyclohex-l-ene-carboxylate (la--ld) are useful chiral building blocks. Novel and efficient syntheses of these four epoxy chiral building blocks from naturally abun- dant (--)-shikimic acid (2) via cyclic sulfite intermediates are described in this article. The targeted compound (3R,4R,5S)-la was synthesized via four steps from (--)-shikimic acid in 79% overall yield. The other three targeted compounds (3S,4R,5S)-lb, (3S,4S,5R)-1c and (3R,4S,5R)-ld were synthesized via seven steps from (--)-shikimic acid in 56%, 64% and 65% overall yields, respectively.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.201201000