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Methodologies for Synthesis of Cyclotryptamine Alkaloids Me H N N N N H Me N N H Me Min Xie 11/20/2007 Nomenclature NH NH H N H N COOH 2 2 Tryptophan Tryptamine -Biosynthetic intermediate -Neurotransmitter Me Me H H H H N N R N N 4 3b 3a 3 5 6 8 1 2 N N 7b 8a 7 H R' N N N N H H H H Me Me cyclotryptamine (-)-chimonanthine meso-chimonanthine Higher-order Cyclotryptamine Alkaloids Me Me H H H H N N N N Me H H N N N N H H Me N N N N H H H H Me Me (-)-hodgkinsine N N H H Me (-)-quadrigemine C From Psychotria colorata - antibacterial Non-peptide antagonist of the somatostatin. - analgesic Rasolonjanahary, Sevenet, Voegelein, Kordon， Eur. J. Pharm. 1995, 285, 19. Somatostatin: peptide hormone - regulates the endocrine system - affects neurotransmission and cell proliferation (wikipedia) Question Me H H N N ? + H N N H H Me (-)-chimonanthine 2 H O 2 H O 2 2 Isomeric Natural Products Me H H N N Me H H N N + H N N H H Me N N H H Me (-)-quadrigemine C Structural Features of Cyclotryptamine Alkaloids • Repeated Pyrollindinoindoline units • Pyrolidine Me H H Cis configuration N N N-methylated • Vincinal quaternary C centers N N H H Me • Benzylic-benzylic or C7- N N H H Me benzylic linkage (-)-hodgkinsine • Elongated C3a-C3a’ σ bond Synthetic challenge: • Stereocontrolled construction of vicinal quarternary carbon centers. • Construction of diaryl quarternary carbon centers. • Construction of pyrollindino[2,3-b]indoline scaffold. • Mild conditions to maintain labile C3a-C3a’ s bond. Isotope Labeling Experiment * Me T H N T NH 2 N N H * [β-14C, 2-3H]tryptamine Chimonanthus fragrans 3H:14C = 4.20 * N N COOH * H T Me (-)-chimonanthine N T NH 2 H rac AcOH [β-14C, 2-3H]tryptophan 3H:14C = 4.35 MeT H N N * * tryptamine incorporation 11.1% 3H:14C = 4.06 N N H T Me tryptophan incorporation 3.6% 3H:14C = 4.30 (+)-calycathine Kirby, Shah, Herbert, JCS. 1969, 1916 Proposed Biosynthethic Route Oxidative Coupling of Oxindoles H N O NHCO Et 2 NaH, I rac 13% 2 NHCO Et meso 8% 2 THF, rt, hours N O H NHCO Et 2 N O H H Me H N O N N NHCO Et 2 LAH THF, refulx, 24h rac-calycanthine + NHCO Et 2 N N N O H Me 3% 0.2 % H rac-chimonanthine rac Hendrickson, Goschke, Rees,Tetrahedron 1964, 20, 565

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Nomenclature. H2. N. COOH. NH. Tryptophan. H2. N. NH. Tryptamine. N. H. N. R'. R. 1. 2. 3. 3a. 3b. 4. 5. 6. 7. 7b. 8. 8a cyclotryptamine. N. N. H. H. N. N. H. Me. Me. H. (-)-chimonanthine. N. N. H. H. N. N. H. Me. Me. H meso-chimonanthine. -Biosynthetic intermediate. -Neurotransmitter

Methodologies for Synthesis of Cyclotryptamine Alkaloids PDF

38 Pages·2007·1.83 MB·English

by Min Xie

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Nomenclature. H2. N. COOH. NH. Tryptophan. H2. N. NH. Tryptamine. N. H. N. R'. R. 1. 2. 3. 3a. 3b. 4. 5. 6. 7. 7b. 8. 8a cyclotryptamine. N. N. H. H. N. N. H. Me. Me. H. (-)-chimonanthine. N. N. H. H. N. N. H. Me. Me. H meso-chimonanthine. -Biosynthetic intermediate. -Neurotransmitter

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Author:	Min Xie
Publication Year:	2007
Pages:	38
Language:	English
File Size:	1.83
Format:	PDF
Price:	FREE

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