Studies directed toward the total synthesis of discodermolide: asymmetric synthesis of the C1-C14 fragment.
[structure: see text] A convergent and stereoselective assembly of the C1-C14 subunit of marine natural product (+)-discodermolide has been completed. The approach employs chiral allylsilane bond construction methodology to establish four of the eight stereogenic centers. Key fragment coupling is achieved via an efficient stereoselective acetate aldol reaction between C1-C6 and C7-C14 subunits.
Arefolov
Alexander
A
Department of Chemistry and Center for Streamlined Synthesis, Metcalf Center for Science and Engineering, 590 Commonwealth Avenue, Boston University, Boston, Massachusetts 02215, USA.
Panek
James S
JS
D000473:Alkanes; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D002219:Carbamates; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis*; D011161:Porifera / Q000737:chemistry*; D011753:Pyrones; D013237:Stereoisomerism
D000473:Alkanes; D000970:Antineoplastic Agents; D002219:Carbamates; D007202:Indicators and Reagents; D007783:Lactones; D011753:Pyrones; C071229:discodermolide