138906-99-7Relevant articles and documents
The Synthesis and Absolute Configuration of the Novel Ichthyotoxic Diacylglycerols, Umbraculumin A and Umbraculumin C
Medeiros, Edna Faria De,Herbert, John M.,Taylor, Richard J. K.
, p. 2725 - 2730 (2007/10/02)
The total syntheses of umbraculumin A 1 and umbraculumin C 2 in homochiral form are described.Noteworthy steps involve (i) the preparation of the key Z,E-acid 10 by organolithium addition to pyrylium salts, (ii) the use of the 4-methoxyphenylmethyl protecting group for the preparation of 1,2-diacyl glycerols and its removal using trifluoroacetic acid-anisole without significant acyl migration (DDQ removal having proved inefficient) and (iii) a new procedure for the stereoselective preparation of (Z)- and (E)-3-methylthiopropenoic acid.