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Synthesis of 2‐Fluoro Analogues of Frontalin
Author(s) -
Bravo Pierfrancesco,
Frigerio Massimo,
Ono Taizo,
Panzeri Walter,
Pesenti Cristina,
Sekine Akiko,
Viani Fiorenza
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200004)2000:8<1387::aid-ejoc1387>3.0.co;2-g
Subject(s) - chemistry , fluoroacetate , diazomethane , enantiomer , bromide , stereochemistry , toluene , organic chemistry , biochemistry
The synthesis of enantiomerically and diastereomerically pure (−)‐(1 R ,2 R ,5 R )‐ and (−)‐(1 R ,2 S ,5 R )‐2‐fluoro frontalin (7) starting from (+)‐(1 S )‐menthyl‐( R )‐toluene‐4‐sulfinate, methylmagnesium bromide, methyl fluoroacetate, 4‐pentenyl bromide and diazomethane is described. The absolute stereochemistry was unambiguously determined by X‐ray analysis of (+)‐(1 S ,2 R ,5 S,R S )‐ 5 , an intermediate in the synthesis of the enantiomeric (+)‐(1 S ,2 R ,5 S )‐2‐fluoro frontalin (7) .