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Total Synthesis of a Pyrrole Lactone Alkaloid, Longanlactone
Author(s) -
Reddy Chada Raji,
Reddy Motatipally Damoder,
Dilipkumar Uredi
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.201402563
Subject(s) - chemistry , pyrrole , total synthesis , natural product , epimer , yield (engineering) , lactone , organic chemistry , alkaloid , stereochemistry , metallurgy , materials science
The first asymmetric total synthesis of the natural pyrrole lactone longanlactone has been achieved. The key reactions, a Barbier propargylation and a Paal–Knorr pyrrole synthesis, have provided easy access to the target natural product from L ‐aspartic acid in six steps and 31 % overall yield. The C‐4 epimer of the natural product and propionyllonganlactone have also been prepared by this strategy.
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