62410-93-9

Usage

InChI:InChI=1/C20H30O4/c1-2-3-7-10-16(22)12-13-18-17(19(23)15-20(18)24)11-8-5-4-6-9-14-21/h5,8,12-18,22-23H,2-4,6-7,9-11H2,1H3/b8-5-,13-12+/t16-,17+,18+/m0/s1

Upstream product

• 32556-71-1 1-octyn-3-ol 
• 62410-92-8 (3E,11Z)-(1R,2R,5S,14R,15S)-17-Butyl-5-pentyl-6,16,18-trioxa-17-bora-tricyclo[13.3.1.0^2,14]nonadeca-3,11-dien-7-one 
• 62410-94-0 (4E,12Z)-(1S,3R,3aR,6S,14aR)-1-Hydroxy-6-pentyl-3-trimethylsilanyloxy-1,2,3,3a,6,9,10,11,14,14a-decahydro-7-oxa-cyclopentacyclotridecen-8-one 
• 944269-19-6 (3S)-triethylsilyl-1-oxyoctyne 
• 276241-83-9 (1S,2E)-3-[(1R,2R,5R)-5-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-2-(2-butynyl)-3-oxocyclopentyl]-1-pentyl-2-propenyl 5-heptynoate 
• 183073-00-9 (1S,2E)-1-pentyl-3-(1,1,1-tributylstannyl)-2-propenyl (1,1,1-triethylsilyl) ether 
• 276241-81-7 (2R,3R,4R)-4-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-2-(2-butynyl)-3-{(E,3S)-3-[(1,1,1-triethylsilyl)oxy]-1-octenyl}cyclopentan-1-one 
• 276241-84-0 (3S,11aR,14R,14aR)-14-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-3-pentyl-9,10-didehydro-6,7,8,11,11a,13,14,14a-octahydro-3H-cyclopenta[e]oxacyclotridecine-5,12-dione 
• 276241-82-8 (2R,3R,4R)-4-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-2-(2-butynyl)-3-[(E,3S)-3-hydroxy-1-octenyl]cyclopentan-1-one 
• 61305-35-9 (R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone 
• 318234-63-8 (3S,11aR,14R,14aR)-14-hydroxy-3-pentyl-9,10-didehydro-6,7,8,11,11a,13,14,14a-octahydro-3H-cyclopenta[e]oxacyclotridecine-5,12-dione 
• 276241-85-1 (3S,11aR,14R,14aR)-14-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-3-pentyl-6,7,8,11,11a,13,14,14a-octahydro-3H-cyclopenta[e]oxacyclotridecine-5,12-dione 
• 62410-95-1 PGE₂ 1,15-lactone 11-(trimethylsilyl ether) 
• 363-24-6 dinoprostone 

Relevant academic research and scientific papers

Ring-closing alkyne metathesis: Application to the stereoselective total synthesis of prostaglandin E2-1,15-lactone

The first total synthesis of a biologically relevant natural product (prostaglandin E2-1,5-lactone; see picture) by ring-closing diyne metathesis followed by Lindlar reduction is reported. This conceptually novel strategy allows the stereoselective formation of macrocyclic Z alkenes which cannot be accessed stereo-selectively by conventional ring-closing olefin metathesis.

Novel and flexible entries into prostaglandins and analogues based on ring closing alkyne metathesis or alkyne cross metathesis

The suitably functionalized cyclopentanone derivatives 12, 13, 19, and 37 serve as common precursors for the synthesis of various prostaglandins, prostaglandin-1,15-lactones, and unnatural analogues thereof. All of them contain a 2-butynyl entity which is