58030-93-6

Usage

InChI:InChI=1/C19H24O6/c1-9(2)19(22)18(5)15-12(23-16(18)21)6-10(3)11-7-14(20)17(4,24-11)8-13(15)25-19/h6-7,9,12-13,15,22H,8H2,1-5H3/b10-6-

Upstream product

• 137769-70-1 (3S,3aR,4S,6aS)-4-((R)-5-Ethyl-2-methyl-3-oxo-2,3-dihydro-furan-2-ylmethyl)-3-hydroxymethyl-6-isopropylidene-6a-methyl-tetrahydro-furo[3,4-c]furan-1-one 
• 137769-71-2 (3S,3aR,4S,6aS)-4-((R)-5-Ethyl-2-methyl-3-oxo-2,3-dihydro-furan-2-ylmethyl)-3-iodomethyl-6-isopropylidene-6a-methyl-tetrahydro-furo[3,4-c]furan-1-one 
• 137769-64-3 (R)-2-[(S)-2-((2S,3R)-2-Benzyloxymethyl-5-oxo-tetrahydro-furan-3-yl)-2-methoxymethoxy-ethyl]-5-ethyl-2-methyl-furan-3-one 
• 137769-62-1 (R)-2-[(S)-2-((2S,3R)-2-Benzyloxymethyl-5-oxo-tetrahydro-furan-3-yl)-2-hydroxy-ethyl]-5-ethyl-2-methyl-furan-3-one 
• 137769-67-6 (R)-2-[(S)-2-((2S,3R,4S)-2-Benzyloxymethyl-4-isobutyryl-4-methyl-5-oxo-tetrahydro-furan-3-yl)-2-methoxymethoxy-ethyl]-5-ethyl-2-methyl-furan-3-one 
• 137769-66-5 (R)-2-[(S)-2-((2S,3R,4R)-2-Benzyloxymethyl-4-isobutyryl-5-oxo-tetrahydro-furan-3-yl)-2-methoxymethoxy-ethyl]-5-ethyl-2-methyl-furan-3-one 
• 137769-69-8 (3S,3aR,4S,6aS)-3-Benzyloxymethyl-4-((R)-5-ethyl-2-methyl-3-oxo-2,3-dihydro-furan-2-ylmethyl)-6-isopropylidene-6a-methyl-tetrahydro-furo[3,4-c]furan-1-one 
• 137769-75-6 C₁₉H₂₃ClO₇S 
• 137769-74-5 C₁₉H₂₄O₇S 
• 137769-63-2 (R)-2-[2-((2S,3S)-2-Benzyloxymethyl-5-oxo-tetrahydro-furan-3-yl)-2-oxo-ethyl]-5-ethyl-2-methyl-furan-3-one 
• 137769-73-4 C₁₉H₂₄O₅S 
• 137769-60-9 (R)-2-[2-((2S,3R)-2-Benzyloxymethyl-5-oxo-tetrahydro-furan-3-yl)-allyl]-5-ethyl-2-methyl-furan-3-one 
• 137769-53-0 (2S,5R)-5-(2-Bromo-allyl)-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one 
• 137769-52-9 (2R,4R)-4-(2-Bromo-allyl)-2-tert-butyl-4-methyl-5-methylene-[1,3]dioxolane 

Relevant academic research and scientific papers

Asymmetric total synthesis and formal total synthesis of the antitumor sesquiterpenoid (+)-eremantholide A

Figure presented A new asymmetric total synthesis of (+)-eremantholide A is reported in which a Hoveyda-Grubbs ring-closing metathesis (RCM) reaction is used to assemble the nine-membered oxonin ring, and an enolate alkylation between the 3(2H)-furanone 2

Novel Total Synthesis of (+)-Eremantholide A

Stereoselective total synthesis of (+)-eremantholide A (1), a cytotoxic furanoheliangolide sesquiterpene, was accomplished in an enantiospecific fashion.The total synthesis featured the following three key synthetic strategies. (1) Intramolecular cyclization of carbon-radicals derived from xanthates 19a or 19b proceeded regio- and stereoselectively in an exclusive 5-exo-dig mode to provide bicyclic lactones 20a or 20b.Further functional group manipulations of 20a and 20b efficiently afforded a highly substituted 3,7-dioxabicyclooctan-2-one derivative 34, which served as a synthetic equivalent to the A/B ring system in 1. (2) Alkylation of the enolate of 3(2H)-furanone 36 with triflate 35 was thoroughly investigated to maximize formation of the C-alkylated diastereomers, either 10R-isomer 37 or 10S-isomer 38.It was found that choice of the base, solvent, and/or additive was critical to the diastereoselectivity.Furthermore, the 10R-isomer 50 was also prepared in increased yield and improved diastereoselectivity by coupling 36 with A/B ring equivalent 49. (3) In a later stage of the total synthesis, construction of the strained 11-oxabicycloundeca-2,10-dien-9-one system (the C/D) ring) was accomplished by means of an intramolecular vinylogous aldol reaction of aldehyde 52, prepared from 10R-isomer 40, followed by base-catalyzed β-elimination of the corresponding mesylates 54.On the other hand, by employing analogous reaction conditions, the 10S-isomer 56 was transformed into unnatural (-)-10-epi-eremantholide A (61).

A total synthesis of (+)-eramantholide A

Stereoselective and enantiospecific total synthesis of (+)-eremantholide A (1) is described. The present total synthesis features 1) regio- and stereoselective radical carbocyclization of D-glucose-derived γ-lactone 7, and 2) a nine-membered ring formatio