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Total Synthesis of Berkeleyamide A and its 10‐ epi Isomer
Author(s) -
Chakor Narayan S.,
Dallavalle Sabrina,
Scaglioni Leonardo,
Merlini Lucio
Publication year - 2010
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.201000914
Subject(s) - chemistry , total synthesis , aldol reaction , natural product , aldol condensation , stereochemistry , combinatorial chemistry , condensation , penicillium , organic chemistry , catalysis , physics , food science , thermodynamics
A short and efficient synthesis of the novel cytotoxic natural product berkeleyamide A, isolated from a deep‐water Penicillium rubrum , has been accomplished. L ‐Leucinol was used as the only chiral starting material. A diastereoselective aldol condensation is the key step in the synthesis.