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Total Synthesis of (−)‐4a,5‐Dihydrostreptazolin
Author(s) -
Cossy Janine,
Pévet Isabelle,
Meyer Christophe
Publication year - 2001
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 - 10.1002/1099-0690(200108)2001:15<2841::aid-ejoc2841>3.0.co;2-w
Subject(s) - chemistry , acetonide , stereoselectivity , ring closing metathesis , imine , total synthesis , reagent , enyne metathesis , stereochemistry , metathesis , glyceraldehyde , radical cyclization , organic chemistry , triamcinolone acetonide , catalysis , medicine , polymer , surgery , dehydrogenase , polymerization , enzyme
(−)‐4a,5‐Dihydrostreptazolin has been synthesized in nine steps from D ‐glyceraldehyde acetonide. Key steps include a diastereoselective addition of a vinylic Grignard reagent to an imine derived from D ‐glyceraldehyde acetonide, a ring‐closing metathesis, and a stereoselective radical‐mediated enyne cyclization.