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A C 2 ‐Symmetric Pool Based Flexible Strategy: An Enantioconvergent Synthesis of (+)‐Valiolamine and (+)‐Valienamine
Author(s) -
Lo HongJay,
Chen ChengYih,
Zheng WeiLin,
Yeh ShangMing,
Yan TuHsin
Publication year - 2012
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.201101845
Subject(s) - chemistry , tartaric acid , block (permutation group theory) , stereochemistry , organic chemistry , combinatorial chemistry , mathematics , combinatorics , citric acid
A new enantioconvergent strategy directed toward the synthesis of glucosidase inhibitors was developed by using a C 2 ‐symmetric element within the chiral pool and by applying an iodine‐promoted cyclization of an unsaturated carbonimidothioate for the regio‐ and diastereocontrolled installation of amino and hydroxy units. Not only does this simple flexible strategy provide a convergent concise approach to (+)‐valiolamine ( 1 ), but it can also be readily adopted for the synthesis of (+)‐valienamine ( 2 ). Commercially available and cheap C 2 ‐symmetric D ‐tartaric acid served as the chiral building block.