616207-71-7Relevant articles and documents
Total syntheses of Prelactone V and Prelactone B
Raghavendra,Tadiparthi, Krishnaji,Yadav
, p. 17 - 19 (2017/03/15)
The total syntheses of natural products Prelactone-V and Prelactone-B have been accomplished by a novel Chiron approach starting from D-glucose. The synthesis involves isopropylidene acetal formation of D-glucose using Poly(4-vinylpyridine) supported iodine as a catalyst, Tebbe olefination, Grignard reaction, Wittig olefination, selective mono deprotection of acetal using PMA/SiO2, hydrogenation and anti-1,3-diol formation are as key steps.
Total asymmetric syntheses of β-hydroxy-δ-lactones via umpolung with sulfur dioxide
Exner, Claudia J.,Laclef, Sylvain,Poli, Florent,Turks, Maris,Vogel, Pierre
supporting information; experimental part, p. 840 - 845 (2011/04/16)
Cyclic stereotriads and stereotetrads of the β-hydroxy-d-lactone type, e.g. prelactonesBandE, commonin polyketides and polypropionates, are prepared via SO2-induced oxyallylations of enoxysilanes with (1E,3Z)-1-(1-phenylethoxy) penta-1,3-dien-3-yl carboxylates. Using (Z)- or (E)-enoxysilanes both 4,5-cis- or 4,5-trans-d-lactones are obtained. Depending on the reduction method applied to the obtained aldol intermediates 5,6-trans or 5,6-cis-derivatives are formed. The d-lactones can be prepared in both their enantiomeric forms depending on the (1R)- or (1S)-configuration of the starting 1-(1-phenylethoxy)penta-1,3- dienes.
Application of silacyclic allylsilanes to the synthesis of β-hydroxy-δ-lactones: synthesis of Prelactone B
Sellars, Jonathan D.,Steel, Patrick G.
experimental part, p. 5588 - 5595 (2009/12/24)
Silacyclic allylsilanes generated through a silene-diene Diels-Alder cycloaddition represent versatile bifunctional reagents for organic synthesis. This is demonstrated in a short stereocontrolled synthesis of (±)-Prelactone B.