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Daisuke Matsuura 《Tetrahedron letters》2006,47(9):1371-1374
An efficient and stereodefined strategy is described for the asymmetric synthesis of a new styryllactone from the stem bark of Goniothalamus cardiopetalus, cardiobutanolide. The synthetic process is based on requisite manipulation of the functionalized bicyclic lactol-lactone intermediate incorporating the glucuronolactone-derived skeleton in a complete stereoselective manner. 相似文献
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Ashish Garg 《Tetrahedron》2006,62(48):11240-11244
A formal total synthesis of (+)-cardiobutanolide has been accomplished from d-glucose, a readily available precursor. 相似文献
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A chiron approach starting with 3-O-benzyl-1,2-O-isopropylidene-α-d-xylo-pentodialdo-1,4-furanose utilizing a Grignard reaction, Mitsunobu stereoinversion, ethyl diazoacetate addition, and selective reduction of the ketone is employed as a key step for the total synthesis of (+)-cardiobutanolide described; a similar strategy is also reported for the first total synthesis of (+)-3-epi-cardiobutanolide. 相似文献
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Pinki PalArun K. Shaw 《Tetrahedron》2011,67(22):4036-4047
Stereoselective total syntheses of aggregation pheromones (+)-exo-brevicomin (9a), (−)-exo-brevicomin (9b), (+)-endo-brevicomin (9c), (−)-endo-brevicomin (9d) and styryllactones (+)-cardiobutanolide (14a), (−)-cardiobutanolide (14b), and (+)-goniofufurone (19a) were achieved in good yields from enantiomerically pure highly functionalized furanoid glycal building blocks (1a-d) involving similar synthetic strategies, thus making these furanoid glycals highly useful building blocks in diversity-oriented synthesis (DOS). 相似文献
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Ivana Kovačević Mirjana Popsavin Marko V. Rodić Vesna Kojić Velimir Popsavin 《Tetrahedron letters》2019,60(9):684-687
A new asymmetric synthesis of the naturally occurring styryl lactone cardiobutanolide and two novel analogues have been achieved starting from d-xylose. The key steps of the synthesis included an initial zinc mediated reductive THF-ring opening, stereoselective olefination and Sharpless asymmetric dihydroxylation. It was shown that cardiobutanolide (1) exhibits promising in vitro antitumour properties against certain human neoplastic cell lines. It was more potent than the commercial anticancer agent doxorubicin against three cell lines (K562, HL-60 and Raji). 相似文献
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