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Homocoupling in the Preparation of Dimeric Cyclic Peptide Derivatives
Author(s) -
Efskind Jon,
Hope Håkon,
Undheim Kjell
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(20022)2002:3<464::aid-ejoc464>3.0.co;2-j
Subject(s) - chemistry , cyclohexane , stereoselectivity , metathesis , ring closing metathesis , yield (engineering) , substrate (aquarium) , stereochemistry , ring (chemistry) , isopropyl , cyclic peptide , salt metathesis reaction , combinatorial chemistry , peptide , medicinal chemistry , organic chemistry , catalysis , polymerization , biochemistry , materials science , oceanography , metallurgy , geology , polymer
A method for the preparation of dimeric (2 R )‐2,5‐dihydro‐2‐isopropyl‐3,6‐dimethoxypyrazine and 5‐alkenyl derivatives by homocoupling is described. Moderate stereoselectivity was observed. The major product has C 2 ‐symmetry. The course of the stereochemical transformations has been ascertained by a single crystal X‐ray analysis. A C 2 ‐symmetrical bisallyl substrate in a Ru II ‐catalyzed ring‐closing metathesis reaction furnished the corresponding 1,2‐bis(spiroannulated cyclic dipeptido)cyclohexane in >95% yield.