Premium
A Step‐Economic Synthesis of ( S )‐(−)‐Juglomycin C and ( S )‐(−)‐NHAB by Dötz Benzannulation and Convergent Deprotections
Author(s) -
Bhowmik Amit,
Mulay Sandip V.,
Fernandes Rodney A.
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900211
Subject(s) - chemistry , ceric ammonium nitrate , regioselectivity , alkyne , demethylation , epoxide , kinetic resolution , stereochemistry , convergent synthesis , ring (chemistry) , annulation , total synthesis , stereoselectivity , enantioselective synthesis , medicinal chemistry , organic chemistry , catalysis , biochemistry , polymer , gene expression , dna methylation , grafting , gene
A step‐economic stereoselective synthesis of ( S )‐(−)‐juglomycin C and ( S )‐(−)‐NHAB is described. The synthesis features Dötz benzannulation reaction to readily assemble the desired naphthalene structure. The key alkyne fragment was synthesized via a Jacobsen hydrolytic kinetic resolution of racemic epoxide followed by regioselective ring opening. The convergent quinone formation and TBS group removal with ceric ammonium nitrate (CAN) and also AlCl 3 ‐mediated demethylation and tert ‐butyl group removal in a convergent deprotection are notable features in the synthesis.