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Asymmetric Synthesis of the C14–C26 Building Block of Eribulin Mesylate
Author(s) -
Murthy Akondi Srirama,
Mahipal Bodugum,
Chandrasekhar Srivari
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.201201119
Subject(s) - mesylate , chemistry , sharpless asymmetric dihydroxylation , dihydroxylation , eribulin , sulfone , combinatorial chemistry , enantioselective synthesis , aldehyde , block (permutation group theory) , stereochemistry , organic chemistry , cancer , medicine , breast cancer , geometry , mathematics , catalysis , metastatic breast cancer
An alternative route for the synthesis of the C14–C26 building block of the anticancer drug eribulin mesylate is described. The key steps involved in the synthesis are a Julia–Kocienski olefination between aldehyde 4 and sulfone 5 and a tandem Sharpless asymmetric dihydroxylation/S N 2 cyclisation reaction on mesyl compound 3 .