Dihydroxylation-based approach for the asymmetric syntheses of hydroxy-gamma-butyrolactones

Jennifer Peed, Iwan R Davies, Lucy R Peacock, James E Taylor, Gabriele Kociok-Kohn, Steven D Bull

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)
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Abstract

A method of preparing enantiopure hydroxy-gamma-butyrolactones containing multiple contiguous stereocenters in high yield with good diastereoselectivity has been developed. Osmium tetroxide mediated dihydroxylation of a range of beta-alkenyl-beta-hydroxy-N-acyloxazolidin-2-ones results in formation of triols that undergo spontaneous intramolecular 5-exo-trig cyclization reactions to provide hydroxy-gamma-butyrolactones. The stereochemistry of these hydroxy-gamma-butyrolactones has been established using NOE spectroscopy, which revealed that 1-substituted, 1,1-disubstituted, (E)-1,2-disubstituted, (Z)-1,2-disubstituted, and 1,1,2-trisubstituted alkenes undergo dihydroxylation with anti-diastereoselectivity, while 1,2,2-trisubstituted systems afford syn-diastereoisomers. The synthetic utility of this methodology has been demonstrated for the asymmetric synthesis of the natural product 2-deoxy-D-ribonolactone.
Original languageEnglish
Pages (from-to)543-555
Number of pages13
JournalJournal of Organic Chemistry
Volume77
Issue number1
DOIs
Publication statusPublished - 6 Jan 2012

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