Total Synthesis of (−)-Reidispongiolide A, an Actin-Targeting Marine Macrolide†
Ian Paterson Prof. Dr.
University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, UK, Fax: (+44) 1223-336-362 http://www-paterson.ch.cam.ac.uk/
Search for more papers by this authorKate Ashton Dr.
University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, UK, Fax: (+44) 1223-336-362 http://www-paterson.ch.cam.ac.uk/
Search for more papers by this authorRobert Britton Dr.
University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, UK, Fax: (+44) 1223-336-362 http://www-paterson.ch.cam.ac.uk/
Search for more papers by this authorGiuseppe Cecere
University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, UK, Fax: (+44) 1223-336-362 http://www-paterson.ch.cam.ac.uk/
Search for more papers by this authorGaëlle Chouraqui Dr.
University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, UK, Fax: (+44) 1223-336-362 http://www-paterson.ch.cam.ac.uk/
Search for more papers by this authorGordon J. Florence Dr.
University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, UK, Fax: (+44) 1223-336-362 http://www-paterson.ch.cam.ac.uk/
Search for more papers by this authorJonathan Stafford
University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, UK, Fax: (+44) 1223-336-362 http://www-paterson.ch.cam.ac.uk/
Search for more papers by this authorIan Paterson Prof. Dr.
University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, UK, Fax: (+44) 1223-336-362 http://www-paterson.ch.cam.ac.uk/
Search for more papers by this authorKate Ashton Dr.
University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, UK, Fax: (+44) 1223-336-362 http://www-paterson.ch.cam.ac.uk/
Search for more papers by this authorRobert Britton Dr.
University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, UK, Fax: (+44) 1223-336-362 http://www-paterson.ch.cam.ac.uk/
Search for more papers by this authorGiuseppe Cecere
University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, UK, Fax: (+44) 1223-336-362 http://www-paterson.ch.cam.ac.uk/
Search for more papers by this authorGaëlle Chouraqui Dr.
University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, UK, Fax: (+44) 1223-336-362 http://www-paterson.ch.cam.ac.uk/
Search for more papers by this authorGordon J. Florence Dr.
University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, UK, Fax: (+44) 1223-336-362 http://www-paterson.ch.cam.ac.uk/
Search for more papers by this authorJonathan Stafford
University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, UK, Fax: (+44) 1223-336-362 http://www-paterson.ch.cam.ac.uk/
Search for more papers by this authorThis work was supported by the EPSRC (GR/S19929/01), Emmanuel College, Cambridge (Fellowship to G.J.F.), NSERC-Canada (Fellowship to R.B.), Merck Research Laboratories (Scholarship to G.C.), and AstraZeneca. We thank Professor M. V. D'Auria (University of Naples “Federico II”) for providing an authentic sample of natural redispongiolide A and helpful discussions throughout, and Dr. Ray Finlay (AstraZeneca) for assistance.
Graphical Abstract
Actin class: A stereoselective synthesis of the microfilament-destabilizing cytotoxic macrolide (−)-reidispongiolide A, isolated from the marine sponge Reidispongia coerulea, uses a convergent aldol-based strategy to construct the 26-membered macrolactone, followed by a coupling with an N-vinylformamide subunit. This constitutes the first synthesis of any member of the reidispongiolide/sphinxolide family.
Supporting Information
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