Limits...
Catalytic Asymmetric Formal Total Synthesis of ( − )-Triptophenolide and (+)-Triptolide

View Article: PubMed Central - PubMed

ABSTRACT

Abstract: Catalytic asymmetric formal synthesis of (−)-Triptophenolide and (+)-Triptolide have been achieved. Key reaction involves Palladium catalyzed asymmetric conjugate addition of aryl boronic acid to 3-methyl cyclohexe-1-none to form quaternary carbon. Claisen rearrangement and subsequent aldol reaction furnished trans-decaline key intermediate, which assured a formal total synthesis of (−)-Triptophenolide and (+)-Triptolide.

Graphical abstract"/>

Structures of compounds 1–2
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC5385656&req=5

Fig1: Structures of compounds 1–2

Mentions: Tripterygium wilfordii Hook F has long been used to treat rheumatoid arthritis in southern China. The active component was first determined to be Triptolide (TP) (Fig. 1) after it was isolated by Kupchan in 1972 [1]. The unique tri-epoxide moiety attracted numerous attention to identify its molecular mechanism of action in cancer [2–8], immunosuppression [9–11] and contraception [12]. Triptophenolide, a precursor of TP, exhibited potent anti inflammatory and immunosuppressive activity [13, 14].Fig. 1


Catalytic Asymmetric Formal Total Synthesis of ( − )-Triptophenolide and (+)-Triptolide
Structures of compounds 1–2
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5385656&req=5

Fig1: Structures of compounds 1–2
Mentions: Tripterygium wilfordii Hook F has long been used to treat rheumatoid arthritis in southern China. The active component was first determined to be Triptolide (TP) (Fig. 1) after it was isolated by Kupchan in 1972 [1]. The unique tri-epoxide moiety attracted numerous attention to identify its molecular mechanism of action in cancer [2–8], immunosuppression [9–11] and contraception [12]. Triptophenolide, a precursor of TP, exhibited potent anti inflammatory and immunosuppressive activity [13, 14].Fig. 1

View Article: PubMed Central - PubMed

ABSTRACT

Abstract: Catalytic asymmetric formal synthesis of (−)-Triptophenolide and (+)-Triptolide have been achieved. Key reaction involves Palladium catalyzed asymmetric conjugate addition of aryl boronic acid to 3-methyl cyclohexe-1-none to form quaternary carbon. Claisen rearrangement and subsequent aldol reaction furnished trans-decaline key intermediate, which assured a formal total synthesis of (−)-Triptophenolide and (+)-Triptolide.

Graphical abstract"/>