Total synthesis of phorboxazole A. 2. Assembly of subunits and completion of the synthesis.
[Structure: see text] Subunits of phorboxazole A containing C1-C2, C3-C8, C9-C19, C20-C32, C33-C41, and C42-C46 were connected in a sequence that first linked C32 with C33 and then C41 with C42. A C3-C8 fragment was joined to C9-C19, and the assembled unit was then joined with the left half of 1. Closure of the macrolide was accomplished by esterification of the C24 alcohol followed by intramolecular Horner-Wadsworth-Emmons condensation to set the (E)-C2-C3 alkene.
White
James D
JD
Department of Chemistry, Oregon State University, Corvallis, Oregon 97331, USA. james.white@oregonstate.edu
Lee
Tae Hee
TH
Kuntiyong
Punlop
P
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry
D000970:Antineoplastic Agents; D006576:Heterocyclic Compounds, 4 or More Rings; D010080:Oxazoles; C408887:phorboxazole A