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Synthesis and Absolute Configuration of Demethyl (C‐11) Cezomycin
Author(s) -
Li ShaoGang,
Wu Yikang
Publication year - 2013
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201300623
Subject(s) - absolute configuration , cascade , ring (chemistry) , absolute (philosophy) , specific rotation , natural product , stereochemistry , rotation (mathematics) , chemistry , combinatorial chemistry , computer science , organic chemistry , artificial intelligence , chromatography , philosophy , epistemology
The synthesis of (−)‐demethyl (C‐11) cezomycin was achieved through an efficient route that features the use of a Kulinkovich reaction to couple two multifunctionality‐containing fragments and a cascade of ring opening of cyclopropanol/1,5‐hydrogen shift/desilylation–oxidation. The hidden yet undeniable problem of irreproducible specific rotation for this family of compounds was solved by sufficient acidification. The absolute configuration for the natural product was thus established as the mirror image of the synthetic sample.