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Protecting Group Free Formal Total Synthesis of the Antitubercular Agent Erogorgiaene
Author(s) -
Yadav Jhillu S.,
Thirupathaiah, Bodakuntla,
Al Khazim Al Ghamdi Ahmad
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.201101269
Subject(s) - chemistry , total synthesis , enamine , wittig reaction , formal synthesis , intramolecular force , aldol reaction , aldol condensation , protecting group , dehydrogenation , stereochemistry , enantioselective synthesis , combinatorial chemistry , organic chemistry , catalysis , alkyl
Abstract The formal total synthesis of the antitubercular agent erogorgiaene was achieved in 12 steps by using a protecting group free strategy. The synthesis involves an enamine‐mediated 1,4‐addition, an aldol condensation, dehydrogenation, Wittig olefination, intramolecular Friedel–Crafts cyclization, TEMPO‐BAIB‐mediated oxidation, and Evans auxiliary based diastereoselective methylation.