10.1021/acs.orglett.6b03416.s002
Mohammed
K. Abd El-Gaber
Mohammed
K.
Abd El-Gaber
Shigeo Yasuda
Shigeo
Yasuda
Eisuke Iida
Eisuke
Iida
Chisato Mukai
Chisato
Mukai
Enantioselective Total Synthesis of (+)-Sieboldine
A
American Chemical Society
2017
Enantioselective
19 steps
ci
bicyclo
synthesis
hydrindane core
hydroxyazacyclononane ring
Sieboldine
dienyne
late-stage Schmidt glycosylation
Synthesi
quaternary carbon center
Ueno
Pauson
formation
stereoselectivity
sieboldine
enantioselective Keck allylation
methoxybenzyloxy
ee value
2017-01-20 00:00:00
Dataset
https://acs.figshare.com/articles/dataset/Enantioselective_Total_Synthesis_of_-Sieboldine_A/4633279
The first total synthesis of (+)-sieboldine
A was completed starting
from 5-(<i>p</i>-methoxybenzyloxy)pentyne in 19 steps. The
enantioselective Keck allylation provided the dienyne derivative,
which was exposed to the Pauson–Khand conditions to afford
the bicyclo[4.3.0]nonenone derivative with high stereoselectivity
with an ee value of 93%. The following Ueno–Stork reaction
formed the <i>cis</i>-hydrindane core with a quaternary
carbon center. The late-stage Schmidt glycosylation led to the formation
of the <i>N</i>-hydroxyazacyclononane ring.