Evans, Amanda C. and Longbottom, Deborah A. and Matsuoka, Masato and Davies, John E. and Turner, Richard and Franckevicius, Vilius and Ley, Steven V. (2009) Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis. Organic and Biomolecular Chemistry, 7 (4). pp. 747-760. ISSN 1477-0520
Full text not available from this repository.Abstract
A new and efficient desymmetrisation of succinic and glutaric cyclic meso-anhydrides is described, providing excellent yields and diastereoselectivities in most cases. Derivatisation of the desymmetrised products is demonstrated by their conversion into mono-protected 1,4-diols. General synthetic utility of the method is established by its application towards a key fragment in the total synthesis of the immunosuppressant antitumour natural product, rapamycin.