4 years ago

Divergent Asymmetric Total Synthesis of (+)-Vincadifformine, (−)-Quebrachamine, (+)-Aspidospermidine, (−)-Aspidospermine, (−)-Pyrifolidine, and Related Natural Products

Divergent Asymmetric Total Synthesis of (+)-Vincadifformine, (−)-Quebrachamine, (+)-Aspidospermidine, (−)-Aspidospermine, (−)-Pyrifolidine, and Related Natural Products
Nengzhong Wang, Shuo Du, Dong Li, Xuefeng Jiang
A uniformly strategic total synthesis of Aspidosperma alkaloids (+)-vincadifformine, (−)-quebrachamine, (+)-aspidospermidine, (−)-aspidospermine, (−)-pyrifolidine, and nine others from efficiently constructed tricyclic ketone 13 is reported. Highlights of these divergent and practical syntheses include (i) stereoselective intermolecular [4 + 2] cycloaddition to establish a C–E ring with one all-carbon quaternary stereocenter (C-5) and two bridged contiguous cis-stereocenters (C-12 and C-19), (ii) a Pd/C-catalyzed hydrogenation/deprotection/amidation cascade process to assemble the D ring, and (iii) Fischer indolization to forge the A–B ring.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01292

DOI: 10.1021/acs.orglett.7b01292

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