Organocatalytic and Late-Stage CH-Functionalization Enabled Asymmetric Synthesis of Communesin F and Putative Communesins

2017 ◽  
Vol 83 (13) ◽  
pp. 6936-6957 ◽  
Author(s):  
Jisook Park ◽  
Alexandre Jean ◽  
David Y.-K. Chen
Keyword(s):  
Asymmetric Synthesis ◽  
Late Stage ◽  
Communesin F

Diastereoselective Synthesis of (3R,5R)-γ-Hydroxypiperazic Acid

Synlett ◽  
2021 ◽  
Author(s):  
Juan R. Del Valle ◽  
Taylor A. Gerrein ◽  
Yassin M. Elbatrawi
Keyword(s):  
Asymmetric Synthesis ◽  
Late Stage ◽  
Ring Formation ◽  
Peptide Chain ◽  
Nonribosomal Peptides ◽  
Diastereoselective Synthesis ◽  
Hydroxylation Reaction ◽  
Enolate Hydroxylation

AbstractWe report an asymmetric synthesis of the (3R,5R)-γ-hydroxypiperazic acid (γ-OHPiz) residue encountered in several bioactive nonribosomal peptides. Our strategy relies on a diastereoselective enolate hydroxylation reaction and electrophilic N-amination to provide the acyclic γ-OHPiz precursor. This orthogonally protected α-hydrazino acid intermediate is amenable to late-stage diazinane ring formation following incorporation into a peptide chain. We determined the N-terminal amide rotamer propensity of the γ-OHPiz residue and showed that the γ-OH substituent enhances trans-amide bias relative to piperazic acid.

scholarly journals Asymmetric synthesis of (−)-naltrexone

2019 ◽  
Vol 10 (2) ◽  
pp. 535-541 ◽  
Author(s):  
Sun Dongbang ◽  
Blaine Pedersen ◽  
Jonathan A. Ellman
Keyword(s):  
Asymmetric Synthesis ◽  
Late Stage

The asymmetric synthesis of (−)-naltrexone was achieved by a Rh(i)-catalyzed C–H alkenylation and torquoselective electrocyclization cascade and late-stage C–H hydroxylation.

scholarly journals Studies directed toward the exploitation of vicinal diols in the synthesis of (+)-nebivolol intermediates

2017 ◽  
Vol 13 ◽  
pp. 571-578 ◽  
Author(s):  
Runjun Devi ◽  
Sajal Kumar Das
Keyword(s):  
Asymmetric Synthesis ◽  
Antihypertensive Drug ◽  
Late Stage ◽  
Sole Source ◽  
Asymmetric Syntheses ◽  
Asymmetric Dihydroxylation ◽  
Synthetic Utility ◽  
Vicinal Diols ◽  
Saturated Heterocycles

While the exploitation of the Sharpless asymmetric dihydroxylation as the source of chirality in the synthesis of acyclic molecules and saturated heterocycles has been tremendous, its synthetic utility toward chiral benzo-annulated heterocycles is relatively limited. Thus, in the search for wider applications of Sharpless asymmetric dihydroxylation-derived diols for the synthesis of benzo-annulated heterocycles, we report herein our studies in the asymmetric synthesis of (R)-1-((R)-6-fluorochroman-2-yl)ethane-1,2-diol, (R)-1-((S)-6-fluorochroman-2-yl)ethane-1,2-diol and (S)-6-fluoro-2-((R)-oxiran-2-yl)chroman, which have been used as late-stage intermediates for the asymmetric synthesis of the antihypertensive drug (S,R,R,R)-nebivolol. Noteworthy is that a large number of racemic and asymmetric syntheses of nebivolol and their intermediates have been described in the literature, however, the Sharpless asymmetric dihydroxylation has never been employed as the sole source of chirality for this purpose.

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