913556-71-5

Basic information

• Product Name: C₂₈H₂₆N₂O₂S
• Synonyms: C₂₈H₂₆N₂O₂S
• CAS NO: 913556-71-5
• Molecular Weight: 454.593
• Mol File: 913556-71-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₂₈H₂₆N₂O₂S(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₈H₂₆N₂O₂S(913556-71-5)
• EPA Substance Registry System: C₂₈H₂₆N₂O₂S(913556-71-5)

Safety Data

• Hazardous Substances Data: 913556-71-5(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 197143-13-8 (6S,10S)-(-)-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cycloocta[b]indole 
• 7205-94-9 chloromethyl phenyl sulfoxide 
• 4299-70-1 D-Tryptophan methyl ester 
• 84094-74-6 (1S,3R)-(-)-methyl 2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate 
• 63229-68-5 D-(+)-N_bbenzyltryptophan methyl ester 

Downstream Products

• 217448-25-4 (6S,10S)-9-(1'-hydroxy-3'-hexenyl)-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctaindole 
• 217448-31-2 (6S,13S)-4-ethyl-6,7,12,13-tetrahydro-14-(phenylmethyl)-6,13-imino-5H-pyrido[3',4':5,6]cyclooct[1,2-b]indole 
• 217448-27-6 (6S,10S)-8-(1'-ethyl-2'-propenyl)-9-(2',5'-dioxacyclopentanyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole 
• 217448-28-7 (6S,10S)-8-(1'-ethyl-2'-acetyl)-9-(2',5'-dioxacyclopentanyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole 
• 217448-29-8 C₂₆H₂₈N₂O₂ 
• 217448-26-5 (6S,10S)-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde 
• 217448-33-4 (6S,10S)-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde 
• 245760-13-8 C₂₉H₃₆N₂O₄ 
• 245760-13-8 C₂₉H₃₆N₂O₄ 
• 217448-24-3 (6S,10S)-(-)-9-formyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctaindole 

Relevant articles and documents

General approach for the synthesis of sarpagine indole alkaloids. Enantiospecific total synthesis of (+)-vellosimine, (+)-normacusine B, (-)-alkaloid Q3, (-)-panarine, (+)-Na-methylvellosimine, and (+)-Na-methyl-16-epipericyclivine

The first total synthesis of (+)-Na-methyl-16-epipericyclivine (9) was completed [from D-(+)-tryptophan methyl ester] in an overall yield of 42% (eight reaction vessels). The optical rotation [[α]D +22.8 (c 0.50, CHCl3)] obtained on this material confirmed that the reported optical rotation [[α]D 0 (c 0.50, CHCl 3)]47 was biogenetically unreasonable. The total syntheses of (+)-vellosimine, (+)-normacusine B, (-)-alkaloid Q3, (-)-panarine, and (+)-Na-methylvellosimine are also described. Moreover, a mixed sample (1:1) of synthetic (-)-panarine and natural (-)-panarine yielded only one set of signals in the 13C NMR; this indicated that the two compounds are identical and further confirmed the correct configuration of (+)-vellosimine, (+)-normacusine B, and (-)-alkaloid Q3. In this approach, the key templates, (-)-Na-H,N b-benzyltetracyclic ketone 15a and (-)-Na-methyl,N b-benzyltetracyclic ketone 43 were synthesized on multihundred gram scale by the asymmetric Pictet-Spengler reaction and a stereocontrolled Dieckmann cyclization via improved sequences. An intramolecular palladium (enolate-mediated) coupling reaction was employed to introduce the C(19)-C(20) E-ethylidene function in the sarpagine alkaloids for the first time in stereospecific fashion.

The enantiospecific total synthesis of norsuaveoline

Norsuaveoline la has been synthesized enantiospecifically in 28% overall yield from commercially available D-(+)-tryptophan methyl ester via the asymmetric Pictet-Spengler reaction and a stereocontrolled oxy-anion Cope rearrangement as key steps.