The synthesis and absolute configuration of the novel ichthyotoxic diacyiglycerols, umbraculumin A and umbraculumin C
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 11,p. 2725-2730
- https://doi.org/10.1039/p19910002725
Abstract
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.Keywords
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