88023-83-0Relevant articles and documents
Total synthesis of the actinoallolides and a designed photoaffinity probe for target identification
Anketell, Matthew J.,Paterson, Ian,Sharrock, Theodore M.
supporting information, p. 8109 - 8118 (2020/11/03)
The actinoallolides are a family of polyketide natural products isolated from the bacterium Actinoallomurus fulvus. They show potent biological activity against trypanosomes, the causative agents of the neglected tropical diseases human African trypanosomiasis (sleeping sickness) and Chagas disease, while exhibiting no cytotoxicity against human cell lines. Herein, we give a full account of our strategy evolution towards the synthesis of this structurally unique class of 12-membered macrolides, which culminated in the first total synthesis of (+)-actinoallolide A in 20 steps and 8% overall yield. Subsequent late-stage diversification then provided ready access to the congeneric (+)-actinoallolides B-E. Enabled by this flexible and efficient endgame sequence, we also describe the design and synthesis of a photoaffinity probe based on actinoallolide A to investigate its biological mode of action. This will allow ongoing labelling studies to identify their protein binding target(s). This journal is
Total Synthesis of 10-lsocyano-4-cadinene and Determination of Its Absolute Configuration
Nishikawa, Keisuke,Nakahara, Hiroshi,Shirokura, Yousuke,Nogata, Yasuyuki,Yoshimura, Erina,Umezawa, Taiki,Okino, Tatsufumi,Matsuda, Fuyuhiko
supporting information; experimental part, p. 904 - 907 (2010/06/16)
Chemical Equation Presentation The first enantloselective total synthesis of 10-isocyano-4-cadinene, a marine sesquiterpene isolated from nudibranchs of the family Phyllidiidae, was achieved. The cadinene is expected to be a novel nontoxic antifouling agent. In the synthesis, an intermolecular Diels-Alder reaction and a Sml2-induced Barbier-type reaction were employed as key steps. The absolute configuration of 10-isocyano-4-cadinene was determined to be (1S, 6S, 7R, 10S) on the basis of the total synthesis. Antifouling activities against Balanus amphitrite with both enantiomers of 10-isocyano4-cadinene were also evaluated
The palladium-catalyzed enyne cycloisomerization reaction in a general approach to the asymmetric syntheses of the picrotoxane sesquiterpenes. Part I. First-generation total synthesis of corianin and formal syntheses of picrotoxinin and picrotin
Trost, Barry M.,Haffner, Curt D.,Jebaratnam, David J.,Krische, Michael J.,Thomas, Andrew P.
, p. 6183 - 6192 (2007/10/03)
The palladium-catalyzed enyne cycloisomerization is used as a key ring-forming process for the obtention of the cis-fused hydrindane carbon skeleton characteristic of the picrotoxanes sesquiterpenes. The enyne cycloisomerization product is suitably functionalized so that each carbon of the hydrindane core can be modified to permit access to many members of the picrotoxane family, not only to picrotoxinin itself. Part I of this report describes our first-generation approach to the picrotoxane sesquiterpenes as illustrated by the asymmetric synthesis of corianin and the asymmetric formal syntheses of picrotoxinin and picrotin. A new catalyst system to effect the cycloisomerization emerged from this study. Subsequent work proved the generality of this catalyst system.
