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Preparation of (2 E ,4 E ,6 S ,7 S ,10 E ,12 E ,14 S ,15 S ,1′ S )‐7,15‐Bis(1′‐hydroxymethylethyl)‐6,14‐dimethyl‐8,16‐dioxa‐2,4,10,12‐cyclohexadecatetraene‐1,9‐dione. – A Building Block for the Synthesis of Elaiophylin
Author(s) -
Jackson Richard F. W.,
Sutter Marius A.,
Seebach Dieter
Publication year - 1985
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.198519851203
Subject(s) - wittig reaction , chemistry , aldol reaction , isopropyl , stereochemistry , medicinal chemistry , organic chemistry , catalysis
The title compound 2 , which is considered to be a possible key intermediate for a synthesis of the antibiotic elaiophylin ( 1 ), has been obtained by cyclodimerisation of the hydroxy acids 18 and 27 using Yamaguchi's method. The hydroxy acids 18 and 27 are synthesised by Wittig reaction of the (phosphoranylidene)crotonate 14 with the protected 3,5‐dihydroxy‐2,4‐dimethylpentanals 12 and 23 , respectively. These are constructed, in turn, by diastereoselective Evans aldol reaction between ( S )‐3‐benzyloxy‐2‐methylpropanal ( 4 ) and ( R )‐4‐isopropyl‐3‐propionyl‐2‐oxazolidionne.