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Total synthesis of (+/-)-goniomitine via a formal nitrile/donor-acceptor cyclopropane [3 + 2] cyclization.
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 theExpand
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First total synthesis and structural reassignment of (-)-aplysiallene.
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 originalExpand
  • 35
  • 1
Advances in Lewis acid controlled carbon-carbon bond-forming reactions enable a concise and convergent total synthesis of bullatacin.
Lewis acids control regioselectivity in the alkylation of epi-chlorohydrin and the stereochemistry of an alkyne addition to set the C24/C23 anti relationship. These advances facilitate an efficientExpand
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C-2/c-3 annulation and C-2 alkylation of indoles with 2-alkoxycyclopropanoate esters.
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 thisExpand
  • 108
Formal [3 + 2] cycloadditions of donor-acceptor cyclopropanes and nitriles.
  • M. Yu, B. Pagenkopf
  • Chemistry, Medicine
  • Journal of the American Chemical Society
  • 13 June 2003
Donor-acceptor cyclopropanes activated with Me3SiOTf cleave to reactive intermediates that can be efficiently intercepted by nitriles in a formal [3 + 2] dipolar cycloaddition reaction. Aliphatic,Expand
  • 59
A powerful new strategy for diversity-oriented synthesis of pyrroles from donor-acceptor cyclopropanes and nitriles.
Lewis acid activated donor-acceptor cyclopropanes react with aliphatic, aromatic, and alpha,beta-unsaturated nitriles in a novel cascade [3 + 2] dipolar cycloaddition, dehydration, andExpand
  • 67
Mechanistic Insights into Cu-Catalyzed Asymmetric Aldol Reactions: Chemical and Spectroscopic Evidence for a Metalloenolate Intermediate.
In situ IR spectroscopy and transmetalation experiments confirm a postulated catalytic cycle. The metalloenolate 1 describes the active intermediate in the aldol reaction catalyzed by [CuF2Expand
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