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Total Synthesis of (+)‐Aspicilin by an Alkyne‐Based Approach and Its Biological Evaluation
Author(s) -
Raji Reddy Chada,
Rao Nagavaram Narsimha,
Sujitha Pombala,
Kumar Chityal Ganesh
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.201101673
Subject(s) - enyne , alkyne , chemistry , stereoselectivity , total synthesis , sharpless asymmetric dihydroxylation , stereochemistry , hela , dihydroxylation , combinatorial chemistry , enantioselective synthesis , organic chemistry , cell , catalysis , biochemistry
The stereoselective total synthesis of (+)‐aspicilin is described. The pivotal step in this approach is the generation of an enyne intermediate by the coupling of an alkyne with vinyl iodide, which constructed the C6–C7 bond. Conversion of the enyne to the desired macrolide was achieved through Sharpless asymmetric dihydroxylation and Yamaguchi macrolactonization as the key steps. Additionally, the biological activity of (+)‐aspicilin was evaluated on A549, HeLa, and MCF7 cancer cell lines.