1042965-49-0Relevant academic research and scientific papers
Simple stereoselective synthesis of unsaturated lactone intermediates and their conversion into natural dihydropyranones and their enantiomers#
Shinde, Digambar Balaji,Kanth, Boddu Shashi,Satyakumar, Avula,Kamble,Das, Biswanath
, p. 317 - 323 (2013/07/26)
The stereoselective synthesis of the unsaturated lactone intermediates, (S) - and (R)-2-(6-oxo-3, 6-dihydro-2Hpyran-2-yl) acetaldehydes has been accomplished from propane 1,3 diol employing Maruoka asymmetric allylation and ring closing metathesis reaction. The intermediates were converted into two natural dihydropyranones, 6 (R)-4-oxopent-2-enyl 5,6-dihydro-2H-pyran-2-one and (R)- rugulactone and their enantiomers through Wittig olefination.
Total synthesis of (-)-dactylolide and formal synthesis of (-)-zampanolide via target oriented β-C-glycoside formation
Ding, Fei,Jennings, Michael P.
, p. 5965 - 5976 (2008/12/21)
(Chemical Equation Presented) The total synthesis of (-)-dactylolide and formal synthesis of (-)-zampanolide via target oriented β-C-glycoside formation is described. The two key reactions involved a stereoselective reduction of the appropriate oxocarbenium cation and a highly chemo- and diastereoselective ring-closing metathesis protocol for the formation of the macrocyclic core. In addition to the described chemistry, in vitro screening of the antipode of natural dactylolide against the NCI's 60 cancer cell line helped to illuminate the critical importance of the N-acyl hemiaminal side chain of natural zampanolide for its reported potent nanomolar cytotoxicities. Furthermore, by means of the in vitro screen of (-)-dactylolide, a promising cancer therapeutic lead has now emerged for a variety of carcinomas. More specifically, (-)-dactylolide exhibited GI50 values in the nanomolar (25-99 ng/mL) range against the four cell lines HL-60, K-562, HCC-2998, and SF-539, while displaying modest LC50 values.
