Synthesis of (9R,12S)- and (9S,12S)-Cycloisodityrosine and Their N-Methyl Derivatives
- 1 April 1997
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 62 (7) , 2054-2069
- https://doi.org/10.1021/jo961346o
Abstract
Full details of the synthesis of (9R,12S)- and (9S,12S)-cycloisodityrosine and their N-methyl derivatives are detailed based on an intramolecular nucleophilic aromatic substitution reaction for formation of the key biaryl ether with 14-membered ring macrocyclization. Their comparison with prior samples and the documentation of a facile C9 epimerization within the natural 9S series are described.Keywords
This publication has 19 references indexed in Scilit:
- Alternative Synthesis of the Cycloisodityrosine Subunit of Deoxybouvardin, RA-VII, and Related Agents: Reassignment of the Stereochemistry of Prior IntermediatesThe Journal of Organic Chemistry, 1996
- A Synthesis of d,l-N,N-Dimethylcycloisodityrosines: A Comment on the Stereochemistry of Previously Reported Intermediates Related to the Synthesis of RA-VII and DeoxybouvardinThe Journal of Organic Chemistry, 1996
- An unusually facile SnAr 14-membered biaryl ether macrocyclization reaction suitable for preparation of the cycloisodityrosine subunit of bouvardin, deoxybouvardin and related agentsBioorganic & Medicinal Chemistry Letters, 1995
- SNAr-Based Macrocyclization: An Application to the Synthesis of Vancomycin Family ModelsThe Journal of Organic Chemistry, 1994
- Total synthesis of cycloisodityrosine, RA-VII, deoxybouvardin, and N29-desmethyl-RA-VII: Identification of the pharmacophore and reversal of the subunit functional rolesJournal of the American Chemical Society, 1993
- Antitumor Substtance from Higher PlantsHETEROCYCLES, 1993
- Intramolecular Ullmann condensation reaction: an effective approach to macrocyclic diaryl ethersThe Journal of Organic Chemistry, 1991
- The first total synthesis of deoxybouvardin and RA-VII, novel antitumor cyclic hexapeptidesThe Journal of Organic Chemistry, 1987
- Studies on antitumor cyclic hexapeptides RA obtained from Rubiae Radix, Rubiaceae. VI Minor antitumor constituents.CHEMICAL & PHARMACEUTICAL BULLETIN, 1986
- Bouvardin and deoxybouvardin, antitumor cyclic hexapeptides from Bouvardia ternifolia (Rubiaceae)Journal of the American Chemical Society, 1977