320594-06-7

Upstream product

• 320594-03-4 (1R,3aR,4R,5R,7aS)-1-(tert-butyldimethylsilanyloxy)-5-(2,2-dimethoxyethyl)-7a-methyl-3a-(trimethylsilanyloxy)octahydroindene-4-carbaldehyde 
• 168130-60-7 (1R,3aR,4R,5R,7aS)-1-(tert-butyldimethylsilanyloxy)-5-(2,2-dimethoxyethyl)-3a-hydroxy-7a-methyloctahydroindene-4-carbonitrile 
• 168130-61-8 (1R,3aR,4S,5R,7aS)-1-(tert-butyldimethylsilanyloxy)-5-(2,2-dimethoxyethyl)-3a-hydroxy-7a-methyloctahydroindene-4-carbonitrile 
• 168130-62-9 (1R,3aR,4S,5R,7aS)-1-(tert-butyldimethylsilanyloxy)-5-(2,2-dimethoxyethyl)-7a-methyl-3a-(trimethylsilanyloxy)octahydroindene-4-carbonitrile 
• 168130-63-0 (1R,3aR,4S,5R,7aS)-[1-(tert-butyldimethylsilanyloxy)-5-(2,2-dimethoxyethyl)-7a-methyl-3a-(trimethylsilanyloxy)octahydroinden-4-yl]methanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 320594-07-8 (4aR,6aS,7R,9aR,9bS)-7,9a-dihydroxy-6a-methyldecahydrocyclopenta[h]isochromen-3(1H)-one 

Downstream Products

• 320594-08-9 (3RS,4aR,6aS,7R,9aR,9bS)-toluene-4-sulfonic acid 3,9a-dihydroxy-6a-methyldodecahydrocyclopenta[h]isochromen-7-yl ester 

Relevant academic research and scientific papers

Total synthesis of coraxeniolide-A

The first total synthesis of optically active coraxeniolide-A (1a) and 4-epi-coraxeniolide-A (1b) is described. The approach is highly stereoselective and flexible in the preparation of a wide variety of members of the xeniolide family. The use of the Grob-fragmentation was pivotal for the stereospecific elaboration of the nine-membered ring. Coraxeniolide-A (1a) was synthesized in 28 steps by using the Hajos - Parrish diketone 2 as starting material which is available enantiomerically pure.