A Step‐Economic Synthesis of (S)‐(−)‐Juglomycin C and (S)‐(−)‐NHAB by Dötz Benzannulation and Convergent Deprotections. Issue 8 (13th June 2019)

• Record Type: Journal Article
• Authors: Bhowmik, Amit; Mulay, Sandip V.; Fernandes, Rodney A.
• Is Part Of: Asian journal of organic chemistry. Volume 8:Issue 8(2019)
• Page Start: 1534
• Page End: 1538
• Publication Date: 2019-06-13
• Subjects: juglomycins -- antibiotics -- annulation -- stereoselective synthesis -- naphthoquinones; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201900211
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: 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 AlCl3 ‐mediated demethylation and tert ‐butyl group removal in a convergent deprotection are notable features in the synthesis. Abstract : Converging toward success : A step‐economic Dötz benzannulation based synthesis of ( S )‐(−)‐juglomycin C and ( S )‐NHAB has been achieved involving a convergent quinone formation and TBS deprotection using ceric ammonium nitrate and also convergent demethylation and tert ‐butyl group deprotection using AlCl3 .