102209-77-8

Basic information

• Product Name: TELEOCIDINA-2
• Synonyms: TELEOCIDINA-2;(2S,5S)-9-[(S)-1-Ethenyl-1,5-dimethyl-4-hexenyl]-1,2,4,5,6,8-hexahydro-5-(hydroxymethyl)-1-methyl-2-isopropyl-3H-pyrrolo[4,3,2-gh]-1,4-benzodiazonin-3-one;(2S,5S)-9-[(S)-1-Ethenyl-1,5-dimethyl-4-hexenyl]-1,2,4,5,6,8-hexahydro-5-(hydroxymethyl)-1-methyl-2-isopropyl-3H-pyrrolo[4,3,2-gh]-1,4-benzodiazonine-3-one
• CAS NO: 102209-77-8
• Molecular Formula: C₂₇H₃₉N₃O₂
• Molecular Weight: 437.62
• Mol File: 102209-77-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 672.1°C at 760 mmHg
• Flash Point: 360.3°C
• Appearance: /
• Density: 1.064g/cm³
• Vapor Pressure: 5.58E-19mmHg at 25°C
• Refractive Index: 1.56
• PKA: 14.39±0.10(Predicted)
• CAS DataBase Reference: TELEOCIDINA-2(CAS DataBase Reference)
• NIST Chemistry Reference: TELEOCIDINA-2(102209-77-8)
• EPA Substance Registry System: TELEOCIDINA-2(102209-77-8)

Safety Data

• Hazardous Substances Data: 102209-77-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C27H39N3O2/c1-6-9-21-24(28)20-11-12-22(27(5,7-2)13-8-10-17(3)4)25-23(20)18(15-29-25)14-19(16-31)30-26(21)32/h7,10-12,15,19,21,24,29,31H,2,6,8-9,13-14,16,28H2,1,3-5H3,(H,30,32)

Upstream product

• 112775-88-9 (-)-14-O-TBDMS-indolactam-V 
• 84590-48-7 indolactam V 
• 148153-23-5 (10S,13S)-10-Isopropyl-9-methyl-11-oxo-3,9,12-triaza-tricyclo[6.6.1.0^4,15]pentadeca-1,4⁽¹⁵⁾,5,7-tetraene-13-carboxylic acid methyl ester 
• 1097985-47-1 methyl (2S,5R)-2-isopropyl-1-methyl-3-oxo-2,3,4,5,6,8-hexahydro-1H-[1,4]diazonino[7,6,5-cd]indole-5-carboxylate 
• 1271141-46-8 methyl (S)-2-(2-((1H-Indol-4-yl)(methyl)amino)-3-methylbutanamido)acrylate 
• 1638769-41-1 C₃₃H₅₃N₃O₂Si 
• 1638769-40-0 C₃₂H₅₁N₃O₃Si 
• 1638769-38-6 C₃₆H₅₈N₄O₄Si 
• 214267-83-1 (-)-7-bromo-14-O-TBDMS-indolactam-V 
• 102141-01-5 N-methyl-L-valyl-L-tryptophanol 

Downstream Products

• 138424-19-8 (+)-Teleocidin A-1 (+)-MTPA-ester 
• 138424-19-8 (+)-Teleocidin A-2 (+)-MTPA-ester 
• 11032-05-6 teleocidin B-4 
• 95013-42-6 des-O-methyl-olivoretin C 
• 11032-05-6 (-)-teleocidin B-1 
• 109826-72-4 (S)-2-Ethyl-2-methyl-pentanedioic acid bis-[((R)-1-naphthalen-1-yl-ethyl)-amide] 
• 109826-71-3 dimethyl S(-)-α-methyl-α-ethylglutarate 
• 109826-73-5 (S)-2-Ethyl-2-methyl-pentanedioyl dichloride 
• 7769-82-6 (S)-2-Ethyl-2-methyl-pentanedioic acid 
• 109826-72-4 (R)-2-Ethyl-2-methyl-pentanedioic acid bis-[((R)-1-naphthalen-1-yl-ethyl)-amide] 
• 109826-73-5 (R)-2-Ethyl-2-methyl-pentanedioyl dichloride 
• 114446-16-1 (R)-2-Ethyl-2-methyl-pentanedioic acid 
• 109826-70-2 21,22-dihydroteleocidin A-1 
• 109826-70-2 21,22-dihydroteleocidin A-2 

Relevant articles and documents

Total syntheses of indolactam alkaloids (-)-indolactam V, (-)-pendolmycin, (-)-lyngbyatoxin A, and (-)-teleocidin A-2

We report the total syntheses of (-)-indolactam V and the C7-substituted indolactam alkaloids (-)-pendolmycin, (-)-lyngbyatoxin A, and (-)-teleocidin A-2. The strategy for preparing indolactam V relies on a distortion-controlled indolyne functionalization reaction to establish the C4-N linkage, in addition to an intramolecular conjugate addition to build the conformationally-flexible nine-membered ring. The total synthesis of indolactam V then sets the stage for the divergent synthesis of the other targeted alkaloids. Specifically, late-stage sp2-sp3 cross-couplings on an indolactam V derivative are used to introduce the key C7 substituents and the necessary quaternary carbons. These challenging couplings, in addition to other delicate manipulations, all proceed in the presence of a basic tertiary amine, an unprotected secondary amide, and an unprotected indole. Thus, our approach not only enables the enantiospecific total syntheses of four indolactam alkaloids, but also serves as a platform for probing complexity-generating and chemoselective transformations in the context of alkaloid total synthesis. This journal is the Partner Organisations 2014.

Synthesis of Teleocidins A, B and Their Congeners. Part 2. Synthesis of Lyngbyatoxin A (Teleocidin A-1), Teleocidin A-2, Pendolmycin, and (R,E)- and (S,E)-7-(3,7,11-Trimethyl-1,6,10-dodecatrien-3-yl)-(-)-indolactams V

Details of the synthesis method of the tumor promoters, lyngbyatoxin A (= teleocidin A-1) (1) and teleocidin A-2 (2) from (R)- and (S)-methyl N--N-methyl-L-valinate (3 and 4) are presented.Other titled compounds, 6, 7a, and 7b, were prepared analogously. Key words: alkaloid synthesis; lyngbyatoxin A, teleocidin A-2; pendolmycin; teleocidin analogs.