Determination of the relative and absolute configuration of Stigmatellin A by chemical correlation

Author(s):  
Dieter Enders ◽  
Simon Osborne
Author(s):  
Felícia Megumi Ito ◽  
Suély Copini ◽  
Nathália Rodrigues de Almeida ◽  
Kelly Karoliny Lima Pedroni ◽  
Ana Camila Micheletti ◽  
...  

1980 ◽  
Vol 45 (9) ◽  
pp. 2443-2451
Author(s):  
Vladimír Pouzar ◽  
Miroslav Havel

Derivatives of 21-nor-5α-cholane-20,24-diol XI and XIX were prepared by stepwise construction of the side-chain in the position 17β. Their absolute configuration at C(20) was determined on the basis of chemical correlation with the derivatives of 21-nor-5α-cholan-20-ol, XVI and XXIV. The absolute configuration of alcohols XVI and XXIV was determined from the ratio of the yields in which they are formed during the reduction of ketone X and using the benzoate rule. To compounds XI-XVIII the configuration 20R and to compounds XIX-XXVI the configuration 20S has been assigned.


1981 ◽  
Vol 46 (4) ◽  
pp. 917-925 ◽  
Author(s):  
Vladimír Pouzar ◽  
Miroslav Havel

Reaction of the aldehyde I with the lithium salt of 1-(2-tetrahydropyranyloxy)-2-propyne yielded the compounds II and IV. From the compound II the lactone XII was prepared via the intermediates III and X, the lactone XVIII was prepared from the substance IV via the intermediates V and XVI. The unsaturated lactones XII and XVIII were also prepared by sulfenylation and dehydrosulfenylation of the saturated lactones XIII and XIX. Based on chemical correlation and 1H-NMR spectra analyses of the compounds II and IV, the lactone XII was assigned the 20R-configuration whereas the lactone XVIII was allotted the 20S-configuration.


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