Premium
Hexulose Derivatives and Lipase‐Mediated Diastereomeric Resolution in the Enantiospecific Total Synthesis of (−)‐Talaromycins C and E
Author(s) -
Izquierdo Isidoro,
Plaza María T.,
Rodríguez Miguel,
Tamayo Juan A.
Publication year - 2002
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 - 10.1002/1099-0690(20021)2002:2<309::aid-ejoc309>3.0.co;2-v
Subject(s) - chemistry , diastereomer , phosphorane , stereochemistry , undecane , aldehyde , wittig reaction , enantiomer , aldose , lipase , iodide , ketose , organic chemistry , enzyme , catalysis , glycoside
Diastereomeric enzymatic (Chirazyme ® L‐2, c.−f., C2) resolution of 3‐ C ‐acetoxymethyl‐1,2,3,4,5‐pentadeoxy‐6,7:8,9‐di‐ O ‐isopropylidene‐β‐ D ‐ gluco ‐ and ‐ D ‐ manno ‐dec‐6‐ulo‐6,10‐pyranose ( 6 ), obtained from “diacetone D ‐fructose aldehyde” ( 3 ) and the corresponding phosphorane from (3‐benzyloxy‐2‐ethylpropyl)triphenylphosphonium iodide ( 2 ), has enabled us to synthesize spiroketals (3 R ,4 S ,5 S ,6 R ,9 R )‐ and (3 R ,4 S ,5 S ,6 R ,9 S )‐9‐ethyl‐3,4‐isopropylidenedioxy‐1,7‐dioxaspiro[5.5]undecane ( 7 and 8 ). An attempt to transform 8 into (−)‐talaromycins G and 9‐epi‐A was unsuccessful. However, (−)‐talaromycins C and E could be enantiospecifically prepared from spiroketal 7 in twelve steps.