Baars, Julian; Grimm, Isabelle; Blunk, Dirk; Neudorfl, Jorg-Martin; Schmalz, Hans-Guenther published the artcile< Enantioselective Total Synthesis and Structural Revision of Dysiherbol A>, Recommanded Product: But-3-en-1-ol, the main research area is dysiherbol A enantiomer enantioselective synthesis addition cyclization cyclopropane opening; cyclization; enantioselectivity; gold catalysis; natural products; rearrangement.
A 12-step total synthesis of the natural product dysiherbol A, a strongly anti-inflammatory and anti-tumor avarane meroterpene isolated from the marine sponge Dysidea sp., was elaborated. As key steps, the synthesis features an enantioselective Cu-catalyzed 1,4-addition/enolate-trapping opening move, an Au-catalyzed double cyclization to build up the tetracyclic core-carbon skeleton, and a late installation of the C5-bridgehead Me group via proton-induced cyclopropane opening associated with spontaneous cyclic ether formation. The obtained pentacyclic compound I (corresponding to an anhydride of the originally suggested structure for dysiherbol A) showed identical spectroscopic data as the natural product, but an opposite mol. rotation. CD-spectroscopic measurements finally confirmed that both the constitution and the absolute configuration of the originally proposed structure of (+)-dysiherbol A need to be revised.
Angewandte Chemie, International Edition published new progress about 1,4-Addition reaction catalysts (stereoselective). 627-27-0 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H8O, Recommanded Product: But-3-en-1-ol.
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts