639-43-0

Basic information

• Product Name: akuammicine
• Synonyms: akuammicine;(19E)-2,16,19,20-Tetradehydrocuran-17-oic acid methyl ester
• CAS NO: 639-43-0
• Molecular Formula: C₂₀H₂₂N₂O₂
• Molecular Weight: 322.4009
• Mol File: 639-43-0.mol
• Article Data: 22

Chemical Properties

• Melting Point: 182°
• Boiling Point: 480.7°Cat760mmHg
• Flash Point: 244.5°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 2.12E-09mmHg at 25°C
• Refractive Index: 1.661
• PKA: 7.45(at 25℃)
• CAS DataBase Reference: akuammicine(CAS DataBase Reference)
• NIST Chemistry Reference: akuammicine(639-43-0)
• EPA Substance Registry System: akuammicine(639-43-0)

Safety Data

• Hazardous Substances Data: 639-43-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H22N2O2/c1-3-12-11-22-9-8-20-14-6-4-5-7-15(14)21-18(20)17(19(23)24-2)13(12)10-16(20)22/h3-7,13,16,21H,8-11H2,1-2H3/b12-3-/t13-,16-,20+/m0/s1

Upstream product

• 1319726-69-6 C₂₃H₂₈N₂O₃S₂ 
• 50562-79-3 1-(4-tolylsulfonyl)indole-3-carboxaldehyde 
• 1325213-48-6 C₂₀H₂₁IN₂O₃ 
• 1319726-71-0 C₂₀H₂₂BrIN₂O₃ 
• 1319726-70-9 C₁₈H₂₀BrIN₂O 
• 1319726-75-4 C₁₆H₁₉IN₂ 
• 1270076-25-9 C₁₂H₁₄N₂ 
• 1322613-98-8 C₁₆H₁₈N₂O₂ 
• 1320267-37-5 C₂₄H₂₆N₂O₃ 
• 1322613-99-9 methyl (Z)-3-(2-iodobut-2-en-1-yl)-2,3,3a,4,6a,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylate 

Downstream Products

• 38681-90-2 echitamidine 
• 7267-97-2 Methyl-2β,16α,20α-curanoat 
• 7267-97-2 curan-17-oic acid methyl ester 
• 1233498-33-3 (-)-leucoridine C 
• 18397-07-4 (+)-geissoschizoline 
• 56053-17-9 (19E)-2α-cura-16,19-diene 

Relevant articles and documents

Concise total syntheses of (±)-Strychnine and (±)-Akuammicine

Concise total syntheses of Strychnos alkaloids strychnine (1) and akuammicine (2) have been realized in 13 and 6 operations, respectively. Key steps include (1) the vinylogous Mannich reaction; (2) a novel, sequential one-pot spirocyclization/intramolecular aza-Baylis-Hillman reaction; and (3) a Heck cyclization. The synthesis of 1 proceeds via the Wieland-Gumlich aldehyde (26).

Syntheses of Strychnos- and Aspidospermatan-Type Alkaloids. 6. Total Syntheses of (+/-)-Echitamidine, (+/-)-Alstogustine, (+/-)-19-epi-Alstogustine, and (+/-)-Akuammicine

19-Oxodihydroakuammicine was obtained in a three-pot sequence, in 25percent overall yield based on a new condensation-sigmatropic rearrangement sequence.Reductions and quaternization reactions furnished the title compounds.

Catalytic Asymmetric Alkynylation of 3,4-Dihydro-β-carbolinium Ions Enables Collective Total Syntheses of Indole Alkaloids

Chiral tetrahydro-β-carboline (THβC) is not only a prevailing structural feature of many natural alkaloids but also a versatile synthetic precursor for a vast array of monoterpenoid indole alkaloids. Asymmetric synthesis of C1-alkynyl THβCs remains rarely explored and challenging. Herein, we describe the development of two complementary approaches for the catalytic asymmetric alkynylation of 3,4-dihydro-β-carbolinium ions with up to 96 % yield and 99 % ee. The utility of chiral C1-alkynyl THβCs was demonstrated by the collective total syntheses of seven indole alkaloids: harmicine, eburnamonine, desethyleburnamonine, larutensine, geissoschizol, geissochizine, and akuammicine.

Total Synthesis of Strychnine

The total synthesis of the flagship Strychnos indole alkaloid, strychnine, has been accomplished. The developed synthetic sequence features a novel vinylogous 1,4-addition, a challenging iodinium salt mediated silyl enol ether arylation, a palladium-catalyzed Heck reaction, and a streamlined late-stage conversion to strychnine. Furthermore, an application of asymmetric counterion-directed catalysis (ACDC) in the context of target-oriented organic synthesis has been rendered access to an optically active material. The synthetic sequence described herein represents the most concise entry to optically active strychnine to date.