|Stereoselective Synthesis of [4.3.1]Propellane Fragment of Phainanoids A-F|
: 428 : 2018.05.28 00:00
|BULLETIN OF THE KOREAN CHEMICAL SOCIETY|
|Kim, YY (Kim, Yun Yeong); Lee, DH (Lee, Duck-Hyung) 2018.05.01|
Stereoselective Synthesis of [4.3.1]Propellane Fragment of Phainanoids A-F
Kim, YY (Kim, Yun Yeong)[ 1 ] ; Pyun, YM (Pyun, Yu Mi)[ 1 ] ; Jeon, BK (Jeon, Bo Keun)[ 1 ] ; Lee, DH (Lee, Duck-Hyung)[ 1 ]
 Sogang Univ, Dept Chem, Seoul 04107, South Korea.
Phainanoid A (), a triterpenoid compound incorporating a 5,5‐spirocyclic ketal lactone motif and 4,5‐spirocyclic fragment, was isolated along with phainanoids BF (–) from Phyllanthus hainanensis Merr. in 2015 by Professor Yue group (Figure 1). Phainanoids A–F (–) showed strong immunosuppressive activity.For example, phainanoid A () showed higher activity to LPS‐induced B‐cell proliferation test in reference to cyclosporin A (CsA), a well‐known immunosuppressive drug. Recently, two articles regarding the synthesis of 5,5‐spirocyclic ketal lactone motif (C–C) and 4,5‐spirocyclic structure were published. We report herein the stereoselective construction of the [4.3.1]propellane fragment , which would serve as the starting point for the Robinson annulation strategy.