130818-48-3

Usage

InChI:InChI=1/C37H66O8/c1-3-4-5-6-7-8-9-10-11-15-18-31(39)35-23-24-36(45-35)33(41)21-20-32(40)34-22-19-30(44-34)17-14-12-13-16-29(38)26-28-25-27(2)43-37(28)42/h25,27,29-36,38-41H,3-24,26H2,1-2H3

Upstream product

• 790698-17-8 (S)-3-[(R)-7-((2R,5S)-5-{(1S,4R)-1,4-Bis-methoxymethoxy-4-[(2R,5R)-5-((R)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-butyl}-tetrahydro-furan-2-yl)-2-(4-methoxy-benzyloxy)-heptyl]-5-methyl-5H-furan-2-one 
• 206260-14-2 5-(R)-[1-(R)-methoxymethoxy-tridecyl]tetrahydrofuran-2-(R)-carbaldehyde 
• 227186-05-2 (1'R,2R,5R)-5-(hydroxymethyl)-2-<(1'-methoxymethoxy)tridecyl>tetrahydrofuran 
• 661490-54-6 ((R)-1-Benzyloxymethyl-allyloxy)-acetic acid 
• 748770-49-2 4-(S)-benzyl-3-{2-[1-(S)-benzyloxymethyl-allyloxy]acetyl}oxazolidin-2-one 
• 790698-14-5 ((S)-1-Benzyloxymethyl-allyloxy)-acetic acid 
• 790698-12-3 (S)-4-Bromo-2-(4-methoxy-benzyloxy)-pent-4-en-1-ol 
• 790697-91-5 2-(S)-benzyloxymethyl-5-(S)-[1-(S)-methoxymethoxy-prop-2-ynyl]-2,5-dihydrofuran 
• 790697-98-2 3-[3-hydroxy-2-(4-methoxy-benzyloxy)propyl]-5-methyl-5H-furan-2-one 
• 907998-47-4 (R)-1-[(2R,5R)-5-[(R)-1-[triisopropylsilyloxy]tridecyl]tetrahydrofuran-2-yl]prop-2-en-1-ol 
• 1277190-18-7 C₆₁H₁₁₄O₈Si₃ 
• 1277190-19-8 C₆₁H₁₁₈O₈Si₃ 
• 1277190-11-0 dimethyl 2-allyl-2-[(S,2E)-4-[diisopropyl[(R)-1-[(2R,5R)-5-[(R)-1-(triisopropylsilyloxy)tridecyl]-2-tetrahydrofuranyl]allyloxy]silyloxy]-4-[(2S,5S)-5-(2-heptenyl)-2-tetrahydrofuranyl]-2-butenyl]malonate 
• 1277190-14-3 (4S,7R)-4-[(2S,5S)-5-allyl-2-tetrahydrofuranyl]-2,2-diisopropyl-7-[(2R,5R)-5-[(R)-1-(triisopropylsilyloxy)tridecyl]-2-tetrahydrofuranyl]-4,7-dihydro-1,3,2-dioxasilepine 

Relevant academic research and scientific papers

Gonionenin: A new cytotoxic annonaceous acetogenin from Goniothalamus giganteus and the conversion of mono-THF acetogenins to bis-THF acetogenins

A new Annonaceous acetogenin, gonionenin (1), has been isolated from the bark of Goniothalamus giganteus (Annonaceae). C-21/22 double bonds in 1 and in gigantetronenin (10) were oxidized and then cyclized to give pairs of adjacent bis-THF (4 and 7) and nonadjacent bis-THF (11 and 14) acetogenins, respectively. This is the first reported preparation of bis-THF Annonaceous acetogenins through double-bond epoxidation and cyclization from mono-THF acetogenins. The resulting bis-THF compounds (4, 7, 11, 14) showed enhanced bioactivities, versus 1 and 10, with 11 and 14 being over a billion times more cytotoxic than adriamycin against certain solid tumor cell lines.

Allylmalonate as an activator subunit for the initiation of relay ring-closing metathesis reactions

Passing the baton: The relay ring-closing metathesis (RRCM) reaction of complex polyenes 1 has been studied. Several relay subunits (T) were examined and many did not sufficiently activate the RRCM. An allylmalonate-containing relay subunit solved this pr

Sequencing of three-component olefin metatheses: Total synthesis of either (+)-gigantecin or (+)-14-deoxy-9-oxygigantecin

An efficient, flexible, and highly convergent strategy for accessing skipped bis-THF containing Annonaceous acetogenins is demonstrated by the synthesis of each of (+)-gigantecin (1) and its constitutional isomer (+)-14-deoxy-9-oxygigantecin (11). The skeleton of each compound is produced, at will, from the same precursors via a three-component ring-closing/cross- metathesis sequence that differs only in the ordering of the RCM vs CM events. Another notable aspect is the use of in situ epoxide-closing and -opening of iodohydrins with dimethylsulfonium methylide to provide inverted allylic alcohols.

Enantioselective total synthesis of (+)-gigantecin: Exploiting the asymmetric glycolate aldol reaction

The enantioselective synthesis of the potent, selective, cytotoxic, annonaceous acetogenin, (+)-gigantecin, has been completed. An asymmetric glycolate aldol serves to establish the stereocenters at C13,14 and at C21,22. A Carreira asymmetric acetylide ad