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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
An efficient RCM-based synthesis of orthogonally protected meso-DAP and FK565
Juan R Del Valle1, Murray Goodman
1Department of Chemistry and Biochemistry, University of California-San Diego, La Jolla, CA 93027, USA. jdvalle@ucsd.edu
Abstract:
A condensation--ring-close--ring-open sequence was employed for the synthesis of orthogonally protected meso-2,6-diaminopimelic acid, starting from easily accessible chiral synthons. Condensation of suitably protected L-allylglycine and D-vinylglycinol derivatives was followed by Grubbs' ring-closing metathesis to generate the key lactam intermediate. This strategy has been applied to a concise total synthesis of the potent immunostimulatory peptide FK565.
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