174464-92-7Relevant academic research and scientific papers
First construction of a saricandin analog corresponding to papulacandin D
Hamdouchi, Chafiq,Sanchez-Martinez, Concha
, p. 833 - 840 (2007/10/03)
The first total synthesis of a saricandin analog corresponding to papulacandin D has been achieved via a highly convergent synthetic strategy. A readily accessible chiral building block 3 was designed and prepared in large scale via an enantioselective re
Spirocyclic C-glycosides
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, (2008/06/13)
An improved and a new synthetic route for the reparation of spirocyclic C-glycoside compounds having the following general structure are described. STR1 Novel derivatives of spirocyclic C-glycoside compounds are also disclosed which may be used as intermediates in the synthesis and evaluation of potential pharmaceutically active materials.
Total synthesis and structural elucidation of the antifungal agent papulacandin D
Barrett, Anthony G. M.,Pena, Michael,Willardsen, J. Adam
, p. 1082 - 1100 (2007/10/03)
Condensation of the aryllithium reagents, prepared from the bromides 10 and 11 and tert-butyllithium, with lactone 19 and acid-catalyzed spirocyclization gave the papulacandin spiroketals 14 and 15. Subsequent protection using di-tert-butylsilyl bis(trifluoromethanesulfonate) gave the diols 31 and 30. Isoleucine (37) was converted using a double Wittig reaction sequence and propargylation of the intermediate aldehyde 46 into the alkynol 47. Separation of the C-7 epimers of 47 was achieved using kinetic resolution via Sharpless epoxidation. Both alkynol epimers 53 and 57 were converted into the papulacandin side chain esters 65 and 66 using a hydrozirconation and palladium(0)-catalyzed coupling sequence. Comparisons of Mosher ester derivatives of 65 and 66 with the Mosher ester derivative of the natural papulacandin side chain and further degradation were consistent with the stereochemistry of the natural product being 7S,14S. Esterification of the spiroketals with the mixed anhydride 70 and global deprotection gave papulacandin D (1).
Total synthesis of the antifungal agent papulacandin D
Barrett,Pena,Willardsen
, p. 1147 - 1148 (2007/10/02)
Condensation of 2,3,4,6-tetra-O-(trimethylsilyl)-D-gluconolactone with tert-butyl[2-lithio-3,5-di(triisopropylsilyloxy)benzyloxy]dimethylsilane, protection of the resultant spiroketal with di(tert-butyl)silyl di(trifluoromethanesulfonate), selective O-3'-
