Cyclopeptide alkaloids. Synthetic, spectroscopic and conformational studies of phencyclopeptine model compounds

Journal Article · Thu Nov 20 23:00:00 EST 1980 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo01312a001· OSTI ID:6603825

Goff, D; Lagarias, J C; Shih, W C; Klein, M P; Rapoport, H

Peptide cyclization via the p-nitrophenyl ester of 4-methyl-3(4'..beta..-(((N'-((tert-butyloxy)carbonyl)-L-prolyl)amino)ethyl)phenoxy)pentanoic acid (9) has afforded a single cyclopeptide diastereomer, (5S,9R)-9-isopropyl-5,6-trimethylene-8-deamino-1,2-dihydro-p-phencyclopeptine (4), in 36% yield. From the comparative analysis of the uv,ir, circular dichroism (CD), and /sup 1/H NMR spectra of 4 and cyclopeptide (5S)-5,6-trimethylene-8-deamino-1,2-dihydro-p-phencyclopeptine (3d), of known geometry, the conformational identities of the 14-membered ring systems were ascertained. From these data the assignment of R stereochemistry at C9 for cyclopeptide 4 was deduced. Since the stereochemistry at C9 in the naturally occurring phencyclopeptines is the same, these results suggest a feasible route to the stereoselective total synthesis of the phencyclopeptines.

• Research Organization: Univ. of California, Berkeley
• OSTI ID: 6603825
• Journal Information: J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 45:24; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALKALOIDS
CHEMICAL PREPARATION
CIRCULAR CONFIGURATION
CONFIGURATION
DATA
DICHROISM
EXPERIMENTAL DATA
INFORMATION
INFRARED SPECTRA
MAGNETIC RESONANCE
NUCLEAR MAGNETIC RESONANCE
NUMERICAL DATA
ORGANIC COMPOUNDS
PEPTIDES
PROTEINS
RESONANCE
SPECTRA
SYNTHESIS
ULTRAVIOLET SPECTRA