147659-07-2Relevant 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 sulfur ylide mediated epoxidations in the asymmetric synthesis of β-hydroxy-δ-lactones. Synthesis of a mevinic acid analogue and (+)-prelactone B
Aggarwal, Varinder K.,Bae, Imhyuck,Lee, Hee-Yoon
, p. 9725 - 9733 (2007/10/03)
Catalytic and stoichiometric asymmetric sulfur ylide reactions were employed to prepare alkyl-aryl epoxide intermediates in a convergent manner. These epoxides were utilized in efficient syntheses of the mevinic acid analogue 1 and prelactone B. Graphical abstract.