7491-76-1

Usage

InChI:InChI=1/C28H43N3O2/c1-9-27(6)10-11-28(7,17(4)5)20-13-21-22-18(14-29-24(22)23(20)27)12-19(15-32)30-26(33)25(16(2)3)31(21)8/h13-14,16-17,19,25,29,32H,9-12,15H2,1-8H3,(H,30,33)/t19-,25-,27-,28+/m0/s1

Upstream product

• 121587-64-2 Ethyl (αS,6R,9S)-α-amino-6,9-dimethyl-9-ethyl-4-<<(S)-1-(methoxycarbonyl)-2-methylpropyl>methylamino>-6-(1-methylethyl)-6,7,8,9-tetrahydro-1H-benzindole-3-propanoate 
• 121587-59-5 Methyl N-<(6R,9S)-6,9-dimethyl-9-ethyl-6-(1-methylethyl)-6,7,8,9-tetrahydro-1H-benzindol-4-yl>-N-methyl-L-valinate 
• 121587-61-9 Ethyl (6R,9S)-6,9-dimethyl-9-ethyl-α-(hydroxyimino)-4-<<(S)-1-(methoxycarbonyl)-2-methylpropyl>methylamino>-6-(1-methylethyl)-6,7,8,9-tetrahydro-1H-benzindole-3-propanoate 
• 75195-72-1 (S)-2-{[(6R,9S)-3-((S)-2-Amino-3-hydroxy-propyl)-9-ethyl-6-isopropyl-6,9-dimethyl-6,7,8,9-tetrahydro-1H-benzo[g]indol-4-yl]-methyl-amino}-3-methyl-butyric acid 
• 121587-65-3 (S)-2-{[(6R,9S)-3-((S)-2-Amino-3-hydroxy-propyl)-9-ethyl-6-isopropyl-6,9-dimethyl-6,7,8,9-tetrahydro-1H-benzo[g]indol-4-yl]-methyl-amino}-3-methyl-butyric acid methyl ester 

Relevant academic research and scientific papers

Synthesis of teleocidins A, B and their congeners. Part 3. Synthesis of dihydroteleocidin B-4 (dihydroteleocidin B), teleocidin B-3 and teleocidin B-4

Details of the synthesis method of the tumor promoters teleocidin B-3 (3), teleocidin B-4 (4) and dihydroteleocidin B-4 (9) (=dihydroteleocidin B) from (S)- and (R)-methyl N-methyl-N-[7-(3,6,7-trimethyl-1,6-octadien-3-yl)-4-indolyl]-L-valinates (20b and 20a) are presented.

TOTAL SYNTHESIS OF DIHYDROTELEOCIDIN B-4 (DIHYDROTELEOCIDIN B)

A potent tumor promoter, dihydroteleocidin B-4 (= dihydroteleocidin B) (1) was synthesized from L-valine derivative 8 using an acid-catalyzed cyclization of 15 to 16a to construct the teleocidin B structure unit.