Total synthesis of (±)-antroquinonol d.
Total synthesis of (±)-antroquinonol D, which is isolated from very expensive and rarely found Antrodia camphorata and which has potential anticancer properties, was achieved from 4-methoxyphenol. In addition, a Michael addition to dimethoxy cyclohexadienones was studied. The main step involved chelation and substrate-controlled diastereoselective reduction of cyclohexenone and lactonization. Lactone synthesis facilitated the diastereoselective reduction of ketone, which help control the desired stereochemistry at the crucial stereogenic center in the natural product. Other key reactions in the synthesis involved a Michael addition of dimethyl malonate on cyclohexadienone, dihydroxylation, and Wittig olefination. A sesquiterpene side chain was synthesized through coupling with geranyl phenyl sulfide and Bouveault-Blanc reduction.
Department of Chemistry, National Dong-Hwa University , Hualien 97401, Taiwan.
Rohidas S
RS
Sulake
Yan-Feng
YF
Jiang
Hsiao-Han
HH
Lin
Chinpiao
C
Chen
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D055491:Antrodia / Q000737:chemistry*; D001688:Biological Products / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014451:Ubiquinone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D000970:Antineoplastic Agents; D001688:Biological Products; D007783:Lactones; D014451:Ubiquinone; C545357:antroquinonol