JOURNAL ARTICLE
RESEARCH SUPPORT, U.S. GOV'T, NON-P.H.S.
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Total Synthesis of L-156,373 and an oxoPiz Analogue via a Submonomer Approach.

Organic Letters 2018 May 5
The first chemical synthesis of L-156,373 (1), a potent oxytocin receptor antagonist isolated from Streptomyces silvensis, is reported. Assembly of the unusual d-Piz-l-Piz dipeptide subunit was achieved through a sequential electrophilic amination-acylation-deprotection strategy followed by late-stage Piz ring formation. Synthesis and incorporation of a novel N-hydroxy-l-isoleucine building block is also described. This submonomer approach was further applied to the expedient synthesis of a di-δ-oxopiperazic acid analogue of 1 starting from Fmoc-Glu( tBu)-OH building blocks.

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