Synthetic studies of the HIV-1 protease inhibitive didemnaketals: stereocontrolled synthetic approach to the key mother spiroketals.
The stereocontrolled synthesis of (2S,4R,6R,8S,10S,1'R,1' 'R)-2(acetylhydroxymethyl)-4,10-dimethyl-8(isopropenylhydroxymethyl)-1,7-dioxaspiro[5,5]undecane (4a) and its C1' '-epimer (4b), the key mother spiroketals of the HIV-1 protease inhibitive didemnaketals from the ascidian Didemnum sp., has been carried out through multisteps from the natural (R)-(+)-pulegone, which involved the diastereoselective construction of four chiral carbon centers(C-2, C-6, C-8, and C-1') by intramolecular chiral induce.
Jia
Y X
YX
Department of Chemistry & Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.
Wu
B
B
Li
X
X
Ren
S K
SK
Tu
Y Q
YQ
Chan
A S
AS
Kitching
W
W
D000818:Animals; D000081005:Cyclohexane Monoterpenes; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry; D017320:HIV Protease Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D015497:HIV-1 / Q000187:drug effects; D007202:Indicators and Reagents; D008610:Menthol / Q000031:analogs & derivatives / Q000737:chemistry; D039821:Monoterpenes; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014561:Urochordata
D000081005:Cyclohexane Monoterpenes; D003512:Cyclohexanones; D017320:HIV Protease Inhibitors; D007202:Indicators and Reagents; D039821:Monoterpenes; D008610:Menthol; C039648:pulegone