140225-16-7

Upstream product

• 1577-18-0 (E)-3-hexenoic acid 
• 13894-61-6 methyl (E)-hex-3-enoate 
• 876064-67-4 (4R,5S)-5-ethyl-4-hydroxydihydrofuran-2(3H)-one 
• 51236-96-5 (+/-)-methyl trans-3,4-epoxyhexanoate 
• 876064-56-1 (5R,6S)-5-(tert-Butyl-diphenyl-silanyloxy)-oct-1-ene-3,6-diol 
• 876064-55-0 (4R,5S)-4-(tert-Butyl-diphenyl-silanyloxy)-5-ethyl-dihydro-furan-2-one 
• 876064-68-5 (4R,5S)-4-(tert-Butyl-diphenyl-silanyloxy)-5-ethyl-tetrahydro-furan-2-ol 
• 876064-66-3 methyl (+)-(3R,4R)-epoxyhexanoate 
• 137360-05-5 2(R*,S*)-Phenylselenomethyl-4(S*)-ethyl-5(R*)-tert-butyldiphenylsilyloxy-7(R*,S*)-vinyl-1,3-dioxepane 
• 137360-02-2 5(R*)-tert-Butyldiphenylsilyloxy-3(R*,S*),6(S*)-dihydroxy-1-octene 
• 137360-04-4 4(R*)-tert-Butyldiphenylsilyloxy-5(S*)-ethyl-4,5-dihydro-2(3H)-furanone 
• 3285-45-8 4(R*)-Hydroxy-5(S*)-ethyl-4,5-dihydro-2(3H)-furanone 

Downstream Products

• 140170-18-9 (Z,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-hydroxy-4,7,8,9-tetrahydro-3H-oxonin-2-one 
• 71939-43-0 (+)-obtusenyne 
• 876064-59-4 (Z,2S,3R,8R,9S)-3-tert-butyldiphenylsilanyloxy-2-ethyl-8-(4-methoxybenzyloxy)-9-((Z)-5-triisopropylsilanylpent-2-en-4-ynyl)-2,3,4,7,8,9-hexahydrooxonine 
• 876064-75-4 (Z,2S,3R,8R,9S)-3-tert-butyldiphenylsilanyloxy-2-ethyl-8-(4-methoxybenzyloxy)-9-((Z)-5-trimethylsilanylpent-2-en-4-ynyl)-2,3,4,7,8,9-hexahydrooxonine 
• 876064-72-1 (Z,2S,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-2-methansulfonyloxymethyl-3-(4-methoxybenzyloxy)-2,3,4,7,8,9-hexahydrooxonine 
• 1033036-66-6 (Z,2S,3R,8R,9S)-3-tert-butyldiphenylsilanyloxy-2-ethyl-9-((Z)-3-iodoprop-3-enyl)-8-(4-methoxybenzyloxy)-2,3,4,7,8,9-hexahydrooxonine 
• 876064-73-2 (Z,2S,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-2-cyanomethyl-9-ethyl-3-(4-methoxybenzyloxy)-2,3,4,7,8,9-hexahydrooxonine 
• 876064-57-2 (Z,2S,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-2-hydroxymethyl-3-(4-methoxybenzyloxy)-2,3,4,7,8,9-hexahydrooxonine 
• 876064-58-3 (Z,2S,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-2-formylmethyl-3-(4-methoxybenzyloxy)-2,3,4,7,8,9-hexahydrooxonine 
• 876064-71-0 (Z,2S,4aS,6S,7R,11aR)-7-tert-butyldiphenylsilanyloxy-6-ethyl-2-(4-methoxyphenyl)-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxabenzocyclononene 
• 140170-21-4 (Z,2S,3R,8R)-3-tert-butyldiphenylsilanyloxy-2-ethyl-9-methylene-8-trimethylsilanyloxy-2,3,4,7,8,9-hexahydrooxonine 
• 140170-11-2 (Z,2S,3R,8R)-3-tert-butyldiphenylsilanyloxy-8-dimethylsilanyloxy-2-ethyl-9-methylene-2,3,4,7,8,9-hexahydrooxonine 
• 140170-20-3 (Z,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-trimethylsilanyloxy-4,7,8,9-tetrahydro-3H-oxonin-2-one 
• 140170-15-6 (Z,2S,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-hydroxy-2-hydroxymethyl-2,3,4,7,8,9-hexahydrooxonine 

Relevant academic research and scientific papers

A synthesis of (+)-obtusenyne

A synthesis of the halogenated medium-ring ether natural product (+)-obtusenyne is reported utilizing a Claisen rearrangement and an intramolecular hydrosilation as key steps. Georg Thieme Verlag Stuttgart.

Studies Towards the Synthesis of Obtusenyne. A Claisen Rearrangement Approach to Unsaturated Nine-membered Lactones.

An advanced intermediate for the synthesis of the Laurencia oxonane natural product obtusenyne 1, namely the unsaturated nine-membered lactone 3, was efficiently prepared in seven steps from (E)-3-hexenoic acid 7.The key transformation was the Claisen rearrangement of the vinyl ketene acetal 4, which represents novel methodology for the preparation of such unsaturated nine-membered lactones. Key words: medium ring; unsaturated lactone; Claisen rearrangement; vinyl ketene acetal; selenoxide elimination.