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Synthesis of Novel HMG‐CoA Reductase Inhibitors, I. Naphthalene Analogs of Mevinolin
Author(s) -
Novák Lajos,
Rohály JáNos,
Poppe László,
Hornyánszky Gábor,
Kolonits Pál,
Zelei István,
Fehér Imre,
Fekete Jenö,
Szabó Éva,
Záhorszky Uwe,
Jávor András,
Szántay Csaba
Publication year - 1992
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199219920127
Subject(s) - chemistry , reductase , epimer , reagent , yield (engineering) , ylide , alcohol , stereochemistry , tetralones , hmg coa reductase , cofactor , organic chemistry , enzyme , materials science , metallurgy
Abstract The title compounds 2 and their corresponding (6 S ) epimers 18 are prepared in several steps by starting with chiral formyl ester 5 , and α‐tetralones 10 : (1) coupling reaction with the ylide generated from 11 to yield unsaturated ester 13 , (2) reduction to the corresponding alcohol 14 , (3) addition of the Grignard reagent derived from 14 to formyl ester 5 to afford the hydroxy esters 16 and 17 , and (4) lactonization. This procedure is also used to synthesize the β‐naphthyl analogs 29 and 30 . Some results obtained from HMG‐CoA reductase inhibitor screening are also reported.