Synthesis of bistramide A.
We have developed an efficient and highly stereocontrolled synthesis of bistramide A, a selective activator of protein kinase C isotype delta. Our synthetic strategy featured a novel bidirectional approach for spiroketal construction based on the ring-opening/cross-metathesis sequence employing a highly strained cyclopropenone acetal. The synthesis afforded the final target with the longest linear sequence of 15 steps and provided unambiguous structural determination of bistramide A, including assignment of the previously unknown C(37) stereochemistry.
Statsuk
Alexander V
AV
University of Chicago, Department of Chemistry, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
Liu
Dong
D
Kozmin
Sergey A
SA
D000081:Acetamides / Q000138:chemical synthesis*; D000818:Animals; D008387:Marine Toxins / Q000138:chemical synthesis; D011714:Pyrans / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D014561:Urochordata / Q000737:chemistry
D000081:Acetamides; D008387:Marine Toxins; D011714:Pyrans; D013141:Spiro Compounds; C059975:bistratene A