Soaking Up Synthesis

  • Author: David Bradley
  • Published: 14 October 2010
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Organic Letters/ACS Publications
thumbnail image: Soaking Up Synthesis

One of the most fascinating manzamine natural products is nakadomarin A, which was isolated by Kobayashi in 1997 from an Okinawan sponge Amphimedon sp. It has a complex 6/5/5/5/8/15 hexacyclic ring system and embodies a furan ring.

Kobayashi suggested a biosynthetic route to the structure, but now a concise synthesis that includes an enecarbamate Michael addition/furan-N-acyliminium ion cascade cyclization leads to the tetracyclic core. Mark Nilson and Raymond Funk, Pennsylvania State University, USA, then employed a ring-closing alkyne and alkene metatheses which allowed them to construct the fifteen- and eight-membered azacycles, respectively.

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