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Volume 6, Issue 7(Suppl) Med chem
ISSN: 2161-0444 Med chem, an open access journal Stereochemistry 2016
August 18-19, 2016
Page 23
Notes:
conferenceseries.com
Stereochemistry
August 18-19, 2016 Sao Paulo, Brazil
International Conference on
Stereoselective synthesis of (-)-Podophyllotoxin and related lignans through the photocyclization of an axially chiral
3,4-bisbenzylidene succinate amide esters
We have developed a strategy for the stereoselective synthesis of cyclolignans related to podophyllotoxin and its derivatives.
The crucial step of the synthesis is the photocyclization of a chiral atropoisomeric 3,2-bisbenzylidene succinate amide
ester, which can be prepared from the suitable aromatic aldehydes, diethyl succinate and L-prolinol. The photocyclization
was found to be more efficient when the irradiation was performed in a home-built continuous flow photochemical reactor.
The in-flow irradiation also allowed us to perform the reaction on a multigram scale. The chiral auxiliary was removed by
reductive cleavage with the Schwartz’s reagent to give the cytotoxic 1R,2R-cis-podophyllic aldehyde, which in turn could be
easily reduced to the corresponding alcohol, completing the formal synthesis of (-)-podophyllotoxin.
O
O
O
O
OH
H3 CO
OCH3
OCH3
Podophyllotoxin
Biography
Zbigniew Czarnocki obtained his PhD degree from the University of Warsaw (Poland) in 1983. He obtained his habilitation degree (summa cum laude) in 1993 and
in 2002 he became a full Professor. From 1996, he is a Leader of the Laboratory of Natural Products Chemistry. His research interest focuses on stereoselective
synthesis of natural products, modern catalytic reactions and pharmacochemistry of various heterocyclic compounds. He supervised 17 PhD students and has
authored over 120 publications, 6 review articles, 2 book chapters and 6 patents. In 2012, he was appointed as Dean of the Inter-Faculty Studies in Environmental
Protection at the University of Warsaw.
Zbigniew Czarnocki
University of Warsaw, Poland
Zbigniew Czarnocki, Med chem 2016, 6:7(Suppl)