10.1021/acs.orglett.9b01397.s001
Young-In Jo
Young-In
Jo
Martin D. Burke
Martin D.
Burke
Cheol-Hong Cheon
Cheol-Hong
Cheon
Modular Syntheses of Phenanthroindolizidine
Natural Products
American Chemical Society
2019
strategy
hexahydroindolizine
Phenanthro
Subsequent saturation
bromoaryl N
alkaloids
mesyl chloride
Suzuki
dihydroindolizidinium ring
phenanthro
synthesis
Natural
methyliminodiacetate
pyridyl bromide
one-pot
aryl boronic acids
aza-terphenyl
vanadium-catalyzed oxidative electrocyclization
column-separation operations
iterative
MIDA
ortho
Modular Syntheses
boronate
bond
2019-05-21 11:34:38
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Modular_Syntheses_of_Phenanthro_indolizidine_Natural_Products/8159087
A highly concise strategy for the
total synthesis of phenanthroindolizidines
was developed. The one-pot iterative Suzuki–Miyaura reaction
of aryl boronic acids with <i>ortho</i>-bromoaryl <i>N</i>-methyliminodiacetate (MIDA) boronate followed by a second
Suzuki–Miyaura reaction with a suitable pyridyl bromide provided <i>ortho</i>-aza-terphenyls. Subsequent saturation of the triple
bond, treatment with mesyl chloride, and reduction of the resulting
dihydroindolizidinium ring afforded the hexahydroindolizines. A final
vanadium-catalyzed oxidative electrocyclization provided the desired
alkaloids in only three column-separation operations.