Two-Directional Desymmetrization by Double 1,4-Addition of Silicon and Boron Nucleophiles
- 16 April 2012
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 14 (9) , 2406-2409
Abstract
The two-directional desymmetrization of prochiral precursors with α,β-unsaturated branches by catalyst-controlled 1,4-addition of silicon and likewise boron nucleophiles allows for a general enantioselective access to syn,anti-triols with 1,n + 1,2n + 1 (n = 2 and 3) substitution patterns. The utility is demonstrated in the synthesis of the C17–C25 fragment of dermostatin A.Keywords
This publication has 42 references indexed in Scilit:
- Total Synthesis of Dermostatin AThe Journal of Organic Chemistry, 2011
- Total Synthesis of (+)-Roxaticin via C−C Bond Forming Transfer Hydrogenation: A Departure from Stoichiometric Chiral Reagents, Auxiliaries, and Premetalated Nucleophiles in Polyketide ConstructionJournal of the American Chemical Society, 2010
- 1,n‐Glycols as Dialdehyde Equivalents in Iridium‐Catalyzed Enantioselective Carbonyl Allylation and Iterative Two‐Directional Assembly of 1,3‐PolyolsAngewandte Chemie International Edition, 2009
- The Total Synthesis of the Oxopolyene Macrolide RK‐397Angewandte Chemie International Edition, 2007
- Stereochemically General Approach to Adjacent Bis(tetrahydrofuran) Cores of Annonaceous AcetogeninsOrganic Letters, 2006
- Synthetic Efforts toward the C22−C36 Subunit of Halichondrin B Utilizing Local and Imposed SymmetryOrganic Letters, 2005
- Palladium(0)-Mediated Desymmetrization of Meso Tetraols: An Approach to the C3−C17 Bis-oxane Segment of Phorboxazoles A and BOrganic Letters, 2003
- Two-directional synthesis and its use in natural product synthesisTetrahedron, 1995
- Two-directional chain synthesis and terminus differentiationAccounts of Chemical Research, 1994
- Enantiospecific synthesis via sequential diastereofacial and diastereotopic group selective reactions: enantiodivergent synthesis of syn-1,3-polyolsJournal of the American Chemical Society, 1992