ol6b03416_si_002.cif (20.59 kB)
Enantioselective Total Synthesis of (+)-Sieboldine A
dataset
posted on 2017-01-20, 00:00 authored by Mohammed
K. Abd El-Gaber, Shigeo Yasuda, Eisuke Iida, Chisato MukaiThe first total synthesis of (+)-sieboldine
A was completed starting
from 5-(p-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 cis-hydrindane core with a quaternary
carbon center. The late-stage Schmidt glycosylation led to the formation
of the N-hydroxyazacyclononane ring.