P.L. wishes to acknowledge support by the Alexander von Humboldt foundation.
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Communication
Total Synthesis of (+)-Lactiflorin by an Intramolecular [2+2] Photocycloaddition†
Article first published online: 21 DEC 2011
DOI: 10.1002/anie.201106889
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Lu, P. and Bach, T. (2012), Total Synthesis of (+)-Lactiflorin by an Intramolecular [2+2] Photocycloaddition. Angewandte Chemie International Edition, 51: 1261–1264. doi: 10.1002/anie.201106889
- †
Publication History
- Issue published online: 24 JAN 2012
- Article first published online: 21 DEC 2011
- Manuscript Revised: 24 OCT 2011
- Manuscript Received: 28 SEP 2011
Funded by
- Alexander von Humboldt foundation
Keywords:
- cycloaddition;
- glycosylation;
- photochemistry;
- structure elucidation;
- total synthesis
Graphical Abstract
Enlightning synthesis: A light-induced intramolecular [2+2] photocycloaddition reaction (1→2) was the key step in the stereoselective synthesis of (+)-lactiflorin (3) and its triacetate. By comparison with reported analytical data, it was possible to unambiguously elucidate the structure of this natural product, to which three different structures had been previously assigned.