Toward the synthesis of spirastrellolide a: construction of a tetracyclic C26-C40 subunit containing the DEF-bis-spiroacetal.
[reaction: see text] A stereo-controlled synthesis of the fully elaborated C26-C40 tricyclic [5,6,6]-bis-spiroacetal of spirastrellolide A containing the C28 chlorine substituent is reported, exploiting asymmetric Sharpless dihydroxylation and boron-mediated allylation methodology.
Paterson
Ian
I
University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK. ip100@cam.ac.uk
Anderson
Edward A
EA
Dalby
Stephen M
SM
Loiseleur
Olivier
O
D000080:Acetals / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*
D000080:Acetals; D018942:Macrolides; D011083:Polycyclic Compounds; D013141:Spiro Compounds; C475125:spirastrellolide A