Total synthesis of plukenetione A.
We describe an alkylative dearomatization/acid-mediated adamantane annulation sequence that allows facile access to type A polyprenylated acylphloroglucinol natural products including plukenetione A. Introduction of the 2-methyl-1-propenyl moiety was achieved via stereodivergent S(N)2 and S(N)1 cyclizations of allylic alcohol substrates.
Zhang
Qiang
Q
Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, Boston, Massachusetts 02215, USA.
Mitasev
Branko
B
Qi
Ji
J
Porco
John A
JA
D000478:Alkylation; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis*
D011083:Polycyclic Compounds; C534123:plukenetione A