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Total Synthesis of (–)‐Isoamericanin A and (+)‐Isoamericanol A
Author(s) -
Pilkington Lisa I.,
Barker David
Publication year - 2014
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/ejoc.201301363
Subject(s) - chemistry , enantioselective synthesis , lignan , hydroxymethyl , total synthesis , stereochemistry , ring (chemistry) , organic chemistry , catalysis
The enantioselective total synthesis of the biologically active 1,4‐benzodioxane lignans isoamericanin A ( 2 ) and isoamericanol A ( 3 ) has been achieved in 11 and 12 steps, respectively. These benzodioxane lignan natural products, and others that contain 9‐hydroxymethyl group, show a wide range of biological properties. The 1,4‐benzodioxane ring was formed by an acid‐catalysed cyclisation, which gave the desired trans isomer exclusively. This method will allow the synthesis of a number of benzodioxane compounds containing a 9‐hydroxymethyl group