A Step‐Economic Synthesis of ( S )‐(−)‐Juglomycin C and ( S )‐(−)‐NHAB by Dötz Benzannulation and Convergent Deprotections | Zendy

Bhowmik Amit | Zendy; Mulay Sandip V. | Zendy; Fernandes Rodney A. | Zendy

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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.

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