Synthesis of the FGHI Ring System of Azaspiracid

As a causative agent of food poisonings, azaspiracid (1), a novel marine toxin isolated from the mussel Mytilus edulis, challenges the synthetic chemist with an intricate array of acetal and ketal structures. The construction of the FGHI ring system of azaspiracid was achieved by means of a key BF3⋅...

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Published inAngewandte Chemie International Edition Vol. 40; no. 7; pp. 1262 - 1265
Main Authors Nicolaou, K. C., Pihko, Petri M., Diedrichs, Nicole, Zou, Ning, Bernal, Federico
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag GmbH 01.04.2001
WILEY‐VCH Verlag GmbH
Subjects
cyclization
natural products
spiro compounds
synthesis design
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Summary:As a causative agent of food poisonings, azaspiracid (1), a novel marine toxin isolated from the mussel Mytilus edulis, challenges the synthetic chemist with an intricate array of acetal and ketal structures. The construction of the FGHI ring system of azaspiracid was achieved by means of a key BF3⋅Et2O‐catalyzed cyclization to form the HI spirocycle. A final chemoselective intramolecular ketalization with Hg(OAc)2 formed the G ring, to afford the N‐protected FGHI as a single diastereomer.
Bibliography:ark:/67375/WNG-DXVHGCTG-5
istex:997E96E5CE23DF82E34F2758703780ADCA0CE2BD
ArticleID:ANIE1262
We thank Dr. D. H. Huang and Dr. G. Siuzdak for NMR spectroscopic and mass spectrometric assistance, respectively. Financial support for this work was provided by The Skaggs Institute for Chemical Biology, the National Institutes of Health (USA), a predoctoral fellowship from Bristol–Myers Squibb (F.B.), postdoctoral fellowships from the Academy of Finland, the Ella and Georg Ehrnrooth Foundation, and the Tauno Tönning Foundation (all to P.M.P.), ArrayBiopharma (N.Z.), and Bayer AG (N.D.), and grants from Abbott, Amgen, ArrayBiopharma, Boehringer‐Ingelheim, Glaxo, Hoffmann–LaRoche, DuPont, Merck, Novartis, Pfizer, and Schering Plough.
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20010401)40:7<1262::AID-ANIE1262>3.0.CO;2-9