Biomimetic synthesis of polycyclic polyprenylated acylphloroglucinol natural products isolated from Hypericum papuanum.
Biomimetic syntheses of three polycylic polyprenylated acylphloroglucinol natural products isolated from Hypericum papuanum, ialibinone A, ialibinone B, and hyperguinone B, have been accomplished by selective oxidative cyclizations of the proposed biosynthetic precursor 5, which was synthesized from phloroglucinol in three steps.
George
Jonathan H
JH
School of Chemistry & Physics, University of Adelaide, North Terrace, Adelaide SA 5005, Australia. jonathan.george@adelaide.edu.au
Hesse
Micha D
MD
Baldwin
Jack E
JE
Adlington
Robert M
RM
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D003500:Cyclization; D020902:Hypericum / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000737:chemistry*; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification
D001688:Biological Products; D011084:Polycyclic Aromatic Hydrocarbons; C553119:hyperguinone B; C553117:ialibinone A; C553118:ialibinone B; D010696:Phloroglucinol