Corynantheine

Catalog Number	ACM18904546
CAS Number	18904-54-6
Synonyms	(16E)-16,17,18,19-Tetradehydro-17-methoxycorynan-16-carboxylic acid methyl ester
Molecular Weight	366.5
InChI	InChI=1S/C22H26N2O3/c1-4-14-12-24-10-9-16-15-7-5-6-8-19(15)23-21(16)20(24)11-17(14)18(13-26-2)22(25)27-3/h4-8,13-14,17,20,23H,1,9-12H2,2-3H3/b18-13+/t14-,17-,20-/m0/s1
InChI Key	TZUGIFAYWNNSAO-XPOGPMDLSA-N
Purity	95%+
Complexity	604
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	3
Exact Mass	366.1943427
Heavy Atom Count	27
Hydrogen Bond Acceptor Count	4
Hydrogen Bond Donor Count	1
Isomeric SMILES	CO/C=C(\[C@H]1C[C@H]2C3=C(CCN2C[C@@H]1C=C)C4=CC=CC=C4N3)/C(=O)OC
Monoisotopic Mass	366.1943427
PhysicalState	Powder
Rotatable Bond Count	5
Topological Polar Surface Area	54.6 Ų

Case Study

Total Synthesis Strategy of Corynantheine Alkaloids and Related Natural Products

Zhang, Wei, et al. Chemistry-A European Journal, 2011, 17(49), 13814-13824.

High antiviral activity is observed for the indoloquinolizidines of the corynantheine group, dihydrocorynantheine and hirsutine, towards influenza virus type A. The corynantheine family also has anti-inflammatory, anti-arthritic, antibacterial, analgesic, and anti-allergic activities. This work presents an efficient and enantioselective synthetic strategy that allows access to large amounts of optically active quinolizidine alkaloids of the Corynantheine and ipecac families on a multigram scale.
Synthesis strategies and results
· The construction of the core alkaloid skeletons, including the correct absolute and relative stereochemistry, relies on a one-pot cascade sequence that is both enantioselective and diastereodivergent, followed by an additional diastereodivergent reaction step. This method allows for the synthesis of three out of four possible epimers of quinolizidine alkaloids in an enantio- and diastereoselective manner.
· This approach is utilized in the total synthesis of several natural products, including (-)-dihydrocorynantheol, (-)-hirsutinol, (-)-corynantheol, (-)-protometinol, (-)-dihydrocorynantheal, (-)-corynantheal, (-)-protoemetine, (-)-(15S)-hydroxydihydrocorynantheol, and various nonnatural epimers.
· Additionally, this methodology demonstrates its potential in the synthesis of biologically significant natural product analogues that cannot be accessed. Furthermore, the formal synthesis of (+)-dihydrocorynantheine, (-)-emetine, (-)-cephaeline, (-)-tubulosine, and (-)-deoxytubulosine has been reported.

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