143572-82-1

Upstream product

• 191993-30-3 (S)-3-[7-((2R,5S)-5-{(1S,4R)-1-Hydroxy-4-methoxymethoxy-4-[(2R,5R)-5-((R)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-butyl}-tetrahydro-furan-2-yl)-heptyl]-5-methyl-5H-furan-2-one 
• 184435-75-4 (5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one 
• 158664-34-7 2-(1'-benzoyloxy-4'-pentynyl)-5-(1''-methoxymethoxytridecyl)tetrahydrofuran 
• 191993-25-6 (S)-3-(3'-hydroxypropyl)-5-methyl-2,5-dihydrofuran-2-one 
• 191993-42-7 (S)-3-(2'-formylethyl)-5-methyl-2,5-dihydrofuran-2-one 
• 210160-16-0 (S,EZ)-3-(4'-iodo-3'-butenyl)-5-methyl-2,5-dihydrofuran-2-one 
• 191993-23-4 (3RS,5S)-3-(3'-hydroxypropyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one 
• 158664-32-5 (2R,5R,1'R,1R)-2-(1'-hydroxy-4'-butynyl)-5-(1-methoxymethoxytridecyl)tetrahydrofuran 
• 191993-41-6 (3RS,5S)-3-[3'-(tetrahydro-2-pyranyloxy)propyl]-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one 
• 191993-08-5 (2R,5R,1'R,1R)-2-(1'-methoxymethoxy-4'-butynyl)-5-(1-methoxymethoxytridecyl)tetrahydrofuran 
• 191993-13-2 (2R,5R,1'R,8'R,1R,E)-2-(8',9'-epoxy-1'-methoxymethoxy-4'-nonenyl)-5-(1-methoxymethoxytridecyl)tetrahydrofuran 
• 191993-11-0 (2R,5R,1'R,8'S,1R,E)-2-(8',9'-dihydroxy-1'-methoxymethoxy-4'-nonenyl)-5-(1-methoxymethoxytridecyl)tetrahydrofuran 
• 191993-15-4 (2R,5R,1'R,8'R,1R,E)-2-(8'-hydroxy-1'-methoxymethoxy-4'-undecen-10'-ynyl)-5-(1-methoxymethoxytridecyl)tetrahydrofuran 
• 191993-09-6 (2R,5R,1'R,8'S,1R)-2-[8',9'-(1-methylethylidene)dioxy-1'-methoxymethoxy-4'-nonynyl]-5-(1-methoxymethoxytridecyl)tetrahydrofuran 

Relevant academic research and scientific papers

Total synthesis of (+)-4-deoxygigantecin

A total synthesis of a non-adjacent bis-tetrahydrofuranyl annonaceous acetogenin, (+)-4-deoxygigantecin (1) is described. Mono-tetrahydrofuran building block (10), of which the synthesis from (-)-muricatacin (8) had been described in an earlier report, was converted to bis-MOM ether (9) through two-step reactions. Transformation of this compound into non-adjacent bis- tetrahydrofuran unit (5) was carried out by a twelve-step sequence of reactions. Pd(0)-catalyzed cross coupling reaction between 5 and iodinated butenolide (7), which had been prepared from (S)-(-)-ethyl lactate, led to enyne (4). Finally, this compound was converted to (+)-4-deoxygigantecin (1) by two steps.

Total synthesis of (+)-4-deoxygigantecin

(+)-4-Deoxygigantecin (1) was totally synthesized from enantiomerically pure (-)-muricatacin (3). Thus, 3 afforded the key intermediate 5 through a five-step reaction sequence, which was then converted to (+)-4-deoxygigantecin (1) via the formation of bis-tetnhydrofuran unit 11 and a coupling reaction with iodo lactone synthon 16.