143605-56-5

Usage

InChI:InChI=1/C17H28O3/c1-4-13(18)10-15-11(2)9-12-7-5-6-8-14(12)16(15)17(19)20-3/h9,12-16,18H,4-8,10H2,1-3H3/t12-,13-,14-,15+,16+/m1/s1

Upstream product

• 154810-13-6 ethyl (1R,2S,4aR,8aS)-2-<(R)-2-(t-butyldimethylsilyl)oxy>butyl-1,3-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate 
• 154809-99-1 (E)-ethyl 8-(tert-butyldimethylsiloxy)-2-methyl-2-octenoate 
• 154809-97-9 ethyl (2E)-8-hydroxy-2-methyl-2-octenoate 
• 251993-95-0 ethyl 8-hydroxy-2-methyl-2-octenoate 
• 154810-01-2 (E)-2-Methyl-8-oxo-oct-2-enoic acid ethyl ester 
• 109346-75-0 (3R)-3-(tert-butyldimethylsilyloxy)pentanal 
• 109346-74-9 (R)-3-O-(t-butyldimethylsilyl)oxy-1-pentanol 
• 34067-76-0 6-hydroxyhexanal 
• 502-44-3 hexahydro-2H-oxepin-2-one 

Relevant academic research and scientific papers

Total synthesis of PI-201, a new platelet aggregation inhibitor: Establishment of its absolute stereochemistry

Intramolecular Diels-Alder cycloaddition of enantiomerically enriched triene 16 could be attained under thermal conditions resulting in the formation of octahydronaphthalene derivatives 17-20, one of which was converted into PI-201 (1), a new platelet aggregation-inhibitor.

Total syntheses of PI-201 and related compounds

The thermal intramolecular Diels-Alder cycloaddition of a 2:1 mixture of ethyl (2E,8E and Z,10E,13R)-13-(t-butyldimethylsilyl) oxy-2,10-dimethyl-2,8,10-pentadecatrienoate provided four diastereomeric cycloadducts. Deprotection of one of the cycloadducts provided PI-201, a novel platelet aggregation inhibitor, as its natural form. Three stereoisomers of PI-201 were prepared from the other cycloadducts. The intramolecular cycloadditions of some structurally similar trienes were also investigated.