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Full-Text Articles in Physical Sciences and Mathematics
Total Synthesis Of (+/-)-Goniomitine Via A Formal Nitrile/Donor-Acceptor Cyclopropane [3 + 2] Cyclization., Christian L Morales, Brian L Pagenkopf
Total Synthesis Of (+/-)-Goniomitine Via A Formal Nitrile/Donor-Acceptor Cyclopropane [3 + 2] Cyclization., Christian L Morales, Brian L Pagenkopf
Chemistry Publications
The total synthesis of (+/-)-goniomitine has been accomplished in 17 linear steps with 5.2% overall yield starting from commercially available delta-valerolactam. A synthetic highlight includes the first application of a formal [3 + 2] cycloaddition between a highly functionalized nitrile and a donor-acceptor cyclopropane to prepare an indole nucleus. The use of a microwave reactor is shown to greatly improve the reaction times for two steps.
First Total Synthesis And Structural Reassignment Of (-)-Aplysiallene., Jian Wang, Brian L Pagenkopf
First Total Synthesis And Structural Reassignment Of (-)-Aplysiallene., Jian Wang, Brian L Pagenkopf
Chemistry Publications
The first total synthesis of (-)-aplysiallene has been completed in 16 steps and features a key sequential Mukaiyama aerobic oxidative cyclization to prepare the fused bis-THF core. The original stereochemical assignment has been revised as shown.
C-2/C-3 Annulation And C-2 Alkylation Of Indoles With 2-Alkoxycyclopropanoate Esters., Barbora Bajtos, Ming Yu, Hongda Zhao, Brian L Pagenkopf
C-2/C-3 Annulation And C-2 Alkylation Of Indoles With 2-Alkoxycyclopropanoate Esters., Barbora Bajtos, Ming Yu, Hongda Zhao, Brian L Pagenkopf
Chemistry Publications
The annulation reaction between various indoles and 2-alkoxycyclopropanoate esters is reported. Both high efficiency and complete stereochemical control were observed in some cases with this annulation process. A single stereocenter on the cyclopropane controls the diastereoselective formation of up to four new stereocenters. A different reaction course was observed with 3-substituted indole substrates, and an intervening C-3 to C-2-migration process arose that gives synthetically useful C-2 alkylation indole products.