170902-34-8

Upstream product

• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 865091-23-2 (4R)-4-methoxymethoxy-oct-7-enoic acid 
• 865091-48-1 (R)-4-Methoxymethoxy-oct-7-en-1-ol 
• 865091-33-4 Trifluoro-acetic acid (1R,7R)-7-methoxymethoxy-1-{(R)-3-methoxymethoxy-3-[(2R,5R)-5-((S)-1-methoxymethoxy-pentadecyl)-tetrahydro-furan-2-yl]-propyl}-8-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-octyl ester 
• 865091-31-2 (5S,2'R,8'R,11'R,2''R,5''R,1'''S)-5-methyl-3-{2',8',11'-tris(methoxymethoxy)-11'-[5''-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2''-yl]-undecyl}-5H-furan-2-one 
• 53558-93-3 (R)-tetrahydro-5-oxo-2-furancarboxylic acid 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 865091-21-0 (4R,2'R,5'R,1''S)-N-methoxy-4-hydroxy-4-[5'-(1''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-N-methyl-butyramide 
• 865091-34-5 (5R)-5-pentadecanoyl-dihydro-furan-2-one 
• 865091-26-5 (4S,7R,2'R,5'R,1''S)-7-methoxymethoxy-7-[5'-(1''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-hept-1-en-4-ol 
• 151484-76-3 (+)-giganin 
• 471261-23-1 (2S)-toluene-4-sulfonic acid 5-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-pentyl ester 
• 58879-34-8 (S)-5-tosyloxypentan-4-olide 
• 53558-94-4 (R)-(-)-γ-chlorocarbonyl-γ-butyrolactone 

Relevant academic research and scientific papers

Total synthesis and structural confirmation of (+)-longicin

(Chemical Equation Presented) A stereocontrolled total synthesis of (+)-longicin, a representative of the class of mono-THF-acetogenins, is described. The strategy involves the utilization of D- and L-glutamic acids as chirons that correspond to two five-carbon segments harboring stereogenic centers at C4 and at C17 of the C32 polyketide-derived natural product. The use of Grubbs' RCM reaction as a novel "chain elongation" strategy for the synthesis of acetogenin-type structures and a new protocol for butenolide incorporation are also described.

Absolute stereochemistries of giganin and longanin, bioactive non-tetrahydrofuran ring annonaceous acetogenins from Asimina Longifolia

Two cytotoxic Annonaceous acetogenins, giganin (1) and longanin (2), were isolated from the leaves and twigs of Asimina longifolia (Annonaceae). These compounds represent the type of Annonaceous acetogenin lacking either tetrahydrofuran or epoxide rings along the aliphatic chain. Compound (2) is novel and giganin is previously known. The planar structures and absolute configurations of both were elucidated by 1H and 13C nmr and ms before and after certain chemical derivatizations. Compound (2) gave cytotoxic ED50 values comparable to those of adriamycin in a panel of human solid tumor cell lines.