Scalable, catalytic asymmetric synthesis of syn, anti stereotriad building blocks for polypropionate antibiotics.
[reaction: see text] Asymmetric catalysis and chirality transfer by the 2,3-Wittig rearrangement were combined to provide a syn, anti stereotriad-containing olefinic alcohol in five steps from inexpensive starting materials. Development of this compound, a versatile intermediate for polypropionate synthesis, gave known building blocks for discodermolide.
Parker
Kathlyn A
KA
Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York 11794-3400, USA. kparker@notes.cc.sunysb.edu
Cao
Huanyan
H
D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D000970:Antineoplastic Agents; D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000473:Alkanes; D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D002219:Carbamates; D007783:Lactones; D011753:Pyrones; C071229:discodermolide