Asymmetric Synthesis of 1,2,3,4,5,6‐Hexahydro‐5‐hydroxypyrimidin‐2‐ones as Potential HIV‐Protease Inhibitors | Zendy

Enders Dieter | Zendy; Wortmann Lars | Zendy; Dücker Barbara | Zendy; Raabe Gerhard | Zendy

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Asymmetric Synthesis of 1,2,3,4,5,6‐Hexahydro‐5‐hydroxypyrimidin‐2‐ones as Potential HIV‐Protease Inhibitors

Author(s) -

Enders Dieter,

Wortmann Lars,

Dücker Barbara,

Raabe Gerhard

Publication year - 1999

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/(sici)1522-2675(19990804)82:8<1195::aid-hlca1195>3.0.co;2-n

Subject(s) - chemistry , pyrrolidine , alkylation , enantiomer , protease , hiv 1 protease , stereochemistry , enantioselective synthesis , urea , combinatorial chemistry , organic chemistry , enzyme , catalysis

The first asymmetric synthesis of potential cyclic urea HIV protease inhibitors of Type 2 is reported. The synthesis is short and highly versatile in the choice of the substitution pattern and absolute configuration of the products starting from readily available materials. Nonchiral central building block 5 was synthesized and subsequently asymmetrically alkylated under ( R )‐/( S )‐1‐amino‐2‐(methoxymethyl)pyrrolidine (RAMP/SAMP)‐auxiliary control to provide 8a – e . The alkylated ketones then were reduced to the target compounds 9a – e , with good‐to‐excellent overall yields, as well as diastereoisomeric and enantiomeric purities.

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