Corynan-16-carboxylic acid, 16,17,19,20-tetradehydro-17-hydroxy-, methyl ester, (16E,19E)-

Base Information

• Chemical Name: Corynan-16-carboxylic acid, 16,17,19,20-tetradehydro-17-hydroxy-, methyl ester, (16E,19E)-
• CAS No.: 439-66-7
• Molecular Formula: C21H24 N2 O3
• Molecular Weight: 352.433
• Mol file: 439-66-7.mol

Synonyms:Corynan-16-carboxylic acid, 16,17,19,20-tetradehydro-17-hydroxy-, methyl ester, (16E,19E)-

Chemical Property of Corynan-16-carboxylic acid, 16,17,19,20-tetradehydro-17-hydroxy-, methyl ester, (16E,19E)-

Chemical Property:

• Vapor Pressure: 3E-11mmHg at 25°C
• Boiling Point: 528.3°Cat760mmHg
• Flash Point: 273.3°C
• PSA: 62.40000
• Density: 1.26g/cm³
• LogP: 2.95930
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 352.17869263
• Heavy Atom Count: 26
• Complexity: 590

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C1CN2CCC3=C(C2CC1C(C=O)C(=O)OC)NC4=CC=CC=C34
• Isomeric SMILES: CC=C1CN2CCC3=C([C@@H]2C[C@@H]1C(C=O)C(=O)OC)NC4=CC=CC=C34

Technology Process of Corynan-16-carboxylic acid, 16,17,19,20-tetradehydro-17-hydroxy-, methyl ester, (16E,19E)-

There total 86 articles about Corynan-16-carboxylic acid, 16,17,19,20-tetradehydro-17-hydroxy-, methyl ester, (16E,19E)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

Methyl formate (107-31-3) + 20E-[3S*-(3α,15α)]-3,4,5,6,14,15,21-heptahydro-15-(methyl acetate)-20-ethylidene-indolo[2,3-a]quinolizine (32789-73-4) → (Z)-methyl 2-((2S,12bS,E)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-3-hydroxyacrylate (439-66-7)

Guidance literature:

20E-[3S^*-(3α,15α)]-3,4,5,6,14,15,21-heptahydro-15-(methyl acetate)-20-ethylidene-indolo[2,3-a]quinolizine; With n-butyllithium; diisopropylamine; In tetrahydrofuran; at -78 ℃; for 0.5h;

Methyl formate; In tetrahydrofuran; at -78 - 0 ℃; for 5h;

DOI:10.1002/anie.201905227

Reference yield: 73.0%

Methyl formate (107-31-3) + methyl 2-((12b,E)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)acetate (23107-03-1,23107-04-2,32789-73-4,34441-49-1,55903-46-3,101400-33-3,115586-73-7,117772-43-7) → (Z)-methyl 2-((2S,12bS,E)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-3-hydroxyacrylate (439-66-7)

Guidance literature:

methyl 2-((12b,E)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)acetate; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

Methyl formate; at -78 - 0 ℃; for 5h;

DOI:10.1002/anie.201802610

Reference yield:

20E-[3S*-(3α,5β,15α)]-3,4,5,6,14,15,21-heptahydro-15-(methyl acetate)-20-ethylidene-indolo[2,3-a]quinolizine-5-carboxylic acid (236750-92-8) → (Z)-methyl 2-((2S,12bS,E)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-3-hydroxyacrylate (439-66-7)

Guidance literature:

Multi-step reaction with 4 steps

1: N-methylmorpholine / tetrahydrofuran / 0.5 h / -10 - 20 °C

2: NaH / tetrahydrofuran; various solvent(s) / 0.83 h / -10 - 20 °C

3: 167 mg / Bu₃SnH; AIBN / benzene / 4 h / 80 °C

4: 48 percent / LDA

With 4-methyl-morpholine; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; benzene;

DOI:10.1021/ol990554a

upstream raw materials:

20E-[3S^*-(3α,15α)]-3,4,5,6,14,15,21-heptahydro-15-(methyl acetate)-20-ethylidene-indolo[2,3-a]quinolizine

Methyl formate

D-tryptophan

20E-[3S^*-(3α,5β,15α)]-3,4,5,6,14,15,21-heptahydro-15-(methyl acetate)-20-ethylidene-indolo[2,3-a]quinolizine-5-carboxylic acid

Downstream raw materials:

ajmalicine

19-Epiajmalicine

tetrahydroalstonine

16R-E-isositsirikine

Refernces

• 1、 Martin, Stephen F.,Chen, Kevin X.,Eary, C. Todd. "An enantioselective total synthesis of (+)-geissoschizine". . p. 79 - 81. Retrieved 1999.
• 2、 Deiters, Alexander,Chen, Kevin,Eary, C. Todd,Martin, Stephen F.. "Biomimetic entry to the sarpagan family of indole alkaloids: Total synthesis of (+)-geissoschizine and (+)-N-methylvellosimine". . p. 4541 - 4550. Retrieved 2003.
• 3、 Liang, Lixin,Zhou, Shiqiang,Zhang, Wei,Tong, Rongbiao. "Catalytic Asymmetric Alkynylation of 3,4-Dihydro-β-carbolinium Ions Enables Collective Total Syntheses of Indole Alkaloids". . p. 25135 - 25142. Retrieved 2021/10/23.
• 4、 Jarret, Maxime,Turpin, Victor,Tap, Aurélien,Gallard, Jean-Fran?ois,Kouklovsky, Cyrille,Poupon, Erwan,Vincent, Guillaume,Evanno, Laurent. "Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for Enantioselective Total Synthesis of Mavacuran Alkaloids". supporting information. p. 9861 - 9865. Retrieved 2019/07/04.