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A Protection‐Free Synthetic Access to (±)‐1‐Deoxy‐6‐ epi ‐castanospermine and (±)‐1‐Deoxy‐6,8a‐di‐ epi ‐castanospermine
Author(s) -
Serafidou AngelikiTheodora,
Yioti Efthymia G.,
Gallos John K.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201334
Subject(s) - castanospermine , chemistry , dihydroxylation , ether , adduct , stereochemistry , catalysis , organic chemistry , enzyme , enantioselective synthesis
Abstract A new synthesis of (±)‐1‐deoxy‐6‐ epi ‐castanospermine and (±)‐1‐deoxy‐6,8a‐di‐ epi ‐castanospermine has been developed, starting from the hetero‐Diels–Alder adduct of ethyl 2‐nitrosoacrylate and ethyl vinyl ether. Appropriate terminal dienes were prepared by standard manipulations, which, upon RCM followed by dihydroxylation and catalytic Raney Ni hydrogenation, led to the title compounds, which are of significant biological interest. The whole synthesis was completed in eight steps, and no protecting groups were needed in any step.