We thank the New Zealand Foundation for Research, Science and Technology for the award of a Top Achiever Doctoral Scholarship to K.Y.T. and D.C.K.R. We are also grateful to Profs. Y. Kita and Fujioka for providing an authentic sample of 6.
1521-3773/asset/2002_left.gif?v=1&s=ac6b0d94a94d7ce7a210002b8096b42feffc0bcf)
1521-3773/asset/2002_right.gif?v=1&s=451042aa3415ae3ad0729984d26dee1866aca82e)
Communication
An Efficient Formal Synthesis of the Human Telomerase Inhibitor (±)-γ-Rubromycin†
Article first published online: 30 JUL 2009
DOI: 10.1002/anie.200903316
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Rathwell, D., Yang, S.-H., Tsang, K. and Brimble, M. (2009), An Efficient Formal Synthesis of the Human Telomerase Inhibitor (±)-γ-Rubromycin. Angewandte Chemie International Edition, 48: 7996–8000. doi: 10.1002/anie.200903316
- †
Publication History
- Issue published online: 7 OCT 2009
- Article first published online: 30 JUL 2009
- Manuscript Received: 19 JUN 2009
Funded by
- New Zealand Foundation for Research, Science and Technology
Keywords:
- antibiotics;
- azides;
- natural product synthesis;
- spiroketals;
- total synthesis
Graphical Abstract
Balancing act: The correct balance of electronic factors in the naphthazarin and isocoumarin fragments facilitates the acid-mediated spiroketalization step to afford the key densely functionalized spiroketal (see picture; EOM=ethoxymethyl) in the formal synthesis of (±)-γ-rubromycin. A novel regioselective allyloxylation/Claisen rearrangement of 2-azido-1,4-naphthoquinone provides access to the highly oxygenated naphthazarin fragment.