Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis.
A new and efficient desymmetrisation of succinic and glutaric cyclic meso-anhydrides is described, providing excellent yields and diastereoselectivities in most cases. Derivatisation of the desymmetrised products is demonstrated by their conversion into mono-protected 1,4-diols. General synthetic utility of the method is established by its application towards a key fragment in the total synthesis of the immunosuppressant antitumour natural product, rapamycin.
Evans
Amanda C
AC
University of Cambridge, Department of Chemistry, Lensfield Road, Cambridge, UK CB2 1EW.
Longbottom
Deborah A
DA
Matsuoka
Masato
M
Davies
John E
JE
Turner
Richard
R
Franckevicius
Vilius
V
Ley
Steven V
SV
D000812:Anhydrides / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis*; D007166:Immunosuppressive Agents / Q000138:chemical synthesis; D008722:Methods; D020123:Sirolimus / Q000138:chemical synthesis; D013237:Stereoisomerism
D000812:Anhydrides; D001688:Biological Products; D007166:Immunosuppressive Agents; D020123:Sirolimus