TY - JOUR AU - Davy, Jason A.; Moreau, Benoît; Wulff, Jeremy E. TI - Tandem Dihydroxylation, Hemiketalization and Conjugate Addition Leading to a Singly Anomeric Spiroketal SN - 0039-7881 SN - 1437-210X PY - 2012 JO - Synthesis JF - Synthesis LA - EN VL - 44 IS - 12 SP - 1854 EP - 1862 ET - 2012/04/25 DA - 2012/06/05 KW - tandem reaction KW - spiro compounds KW - dihydroxylation KW - stereoselective synthesis KW - enones AB - A novel, highly stereoselective tandem dihydroxylation, hemiketalization and conjugate addition reaction is reported that transforms a linear meso-functionalized bis-enone into a substituted singly anomeric spiroketal, effectively controlling six stereocenters in a single operation. As part of an effort to explore the thermodynamic consequences of establishing the singly anomeric spiroketal in this system, the assembly of a related fully anomeric spiroketal possessing an unusual ketal-spiroketal-ketal framework is demonstrated. PB - © Georg Thieme Verlag DO - 10.1055/s-0031-1290817 UR - http://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0031-1290817 ER -