Asymmetric synthesis of (+)-teratosphaerone B, its non-natural analogue and (+)-xylarenone using an ene- and naphthol reductase cascade. Issue 37 (12th September 2022)

• Record Type: Journal Article
• Authors: Manna, Tanaya; De, Arijit; Nurjamal, Khondekar; Husain, Syed Masood
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 37(2022)
• Page Start: 7410
• Page End: 7414
• Publication Date: 2022-09-12
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob01262f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Bienzyme cascade reduction of putative biosynthetic naphthoquinone substrates give easy access to natural naphthalenones with high yields and high stereoselectivity. Abstract : Herein, a one-pot bienzymatic cascade containing an ene and a naphthol reductase is developed. It is applied for the synthesis of (+)-(3 R, 4 R )-teratosphaerone B, its non-natural regioisomer in both cis - and trans -forms and (+)-xylarenone by the reduction of chemically synthesized naphthoquinone precursors in high yields (76–92%) and excellent ee (>99%). This work implies similar biosynthetic steps in the formation of the synthesized natural products.