1392307-63-9

Upstream product

• 1449483-40-2 (4R,5R,6R,E)-4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6-methyl-9-oxonon-2-enylacetate 
• 1449483-39-9 C₂₈H₄₆O₄Si 
• 1392307-79-7 (E)-ethyl 2-((1R,4R,5S,6R,7R)-6-(benzyloxy)-4-hydroxy-7-methyl-5-vinyl-2-oxabicyclo[2.2.2]octan-3-ylidene)acetate 
• 160488-95-9 (2S,3R)-3,7-dimethyl-6-octene-1,2-diol 
• 106-72-9 (R)-(-)-2,6-dimethyl-5-heptenal 
• 1392307-62-8 (Z)-ethyl 2-((1R,4R,5S,6R,7R)-6-(benzyloxy)-4-hydroxy-7-methyl-5-vinyl-2-oxabicyclo[2.2.2]octan-3-ylidene)acetate 
• 1392307-60-6 ethyl 3-((1R,2S,3R,4R,5R)-3-(benzyloxy)-1,4-dihydroxy-5-methyl-2-vinylcyclohexyl)propiolate 
• 1392307-57-1 (2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanone 
• 1392307-56-0 ((E)-((2R,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexylidene)methoxy)triisopropylsilane 
• 1392307-53-7 ((4R,5R,6R,(E))-4-(benzyloxy)-1-bromo-6,10-dimethylundeca-2,9-dien-5-yloxy)(tert-butyl)dimethylsilane 
• 1392307-52-6 (4R,5R,6R,(E))-4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dien-1-ol 
• 1392307-51-5 (4R,5R,6R,(E))-ethyl 4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dienoate 
• 1392307-50-4 (2R,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-en-1-ol 
• 1392307-55-9 (2R,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanecarbaldehyde 

Downstream Products

• 1392307-74-2 (5R,7S,(9E),10aR,11R,12R,13R,14aR)-11-benzyloxy-5,6,7,8,11,12,13,14-octahydro-8-hydroxy-4-(methoxymethoxy)-5,7,13-trimethyl-12,14a,3-(epoxymethino)-2H-1-benzoxacyclododecyn-2-2(4H,10aH)-one 
• 1392307-75-3 (5R,7S,(9E),10aR,11R,12R,13R,14aR)-11-(benzyloxy)-6,7,11,12,13,14-hexahydro-5,7,13-trimethyl-12,14a,3-(epoxymethino)-2H-1-benzoxacyclododecyn-2,4,8(5H,10aH)-trione 
• 1449483-73-1 (3S,5R,7S,9E,10aR,11R,12R,13R,14aR)-4-chloro-11-(benzyloxy)-6,7,11,12,13,14-hexahydro-5,7,13-trimethyl-12,14a,3-(epoxymethyno)-2H-1-benzoxacyclododecin-2,8(5H,10aH)-dione 
• 1449483-74-2 (4S,5R,7S,9E,10aR,11R,12R,13R,14aR)-11-(benzyloxy)-5,6,7,11,12,13,14-pentahydro-4-(methoxymethoxy)-5,7,13-trimethyl-12,14a,3-(epoxymethyno)-2H-1-benzoxacyclododecin-2,8(5H,10aH)-dione 
• 1449483-75-3 (4R,5R,7S,9E,10aR,11R,12R,13R,14aR)-11-(benzyloxy)-5,6,7,11,12,13,14-pentahydro-4-(methoxymethoxy)-5,7,13-trimethyl-12,14a,3-(epoxymethyno)-2H-1-benzoxacyclododecin-2,8(5H,10aH)-dione 

Relevant academic research and scientific papers

Total synthesis and biological evaluation of (-)-atrop-abyssomicin C

Enantioselective synthesis of a marine antibiotic (-)-atrop-abyssomicin C was accomplished in 21 steps, in 1.8% overall yield (4%, based on the recovered starting material). The key steps of the synthesis are the formation of the functionalized cyclohexane core by an organocatalyzed Tsuji-Trost reaction, the formation of a tricyclic spirotetronate unit by a gold-catalyzed reaction sequence and the highly efficient eleven-membered ring closure by a Nozaki-Hiyama-Kishi reaction. Biological tests showed all abyssomicin derivatives to possess strong antibacterial activity against methicillin resistant S. aureus strains; however, they also proved to be cytotoxic, both to malignant and to normal somatic cells. The Royal Society of Chemistry.

Total synthesis of (-)-atrop-abyssomicin C

Rolling in the deep: An enantioselective synthesis of a marine antibiotic (-)-atrop-abyssomicin C (see scheme) is described. The key steps of the synthetic sequence are the application of dual catalysis in the formation of the cyclohexane core, the gold-catalyzed formation of a tricyclic spirotetronate unit, and a highly efficient eleven-membered ring closure by a Nozaki-Hiyama-Kishi reaction. Copyright