Total Synthesis of Antascomicin B (pages 2732–2737)
Dominic E. A. Brittain, Charlotte M. Griffiths-Jones, Michael R. Linder, Martin D. Smith, Catherine McCusker, Jaqueline S. Barlow, Ryo Akiyama, Kosuke Yasuda and Steven V. Ley
Article first published online: 1 APR 2005 | DOI: 10.1002/anie.200500174
The structurally enticing antascomicin B (1), which exhibits potent immunosuppressant-antagonizing properties, has a complex polyketide structure. Key steps in its enantioselective total synthesis include a transannular catechol-templated Dieckmann reaction to assemble the challenging tricarbonyl functionality and a butanediacetal-directed allylation.