A Biomimetic Synthesis of Racemic Dihydroanthracen‐1(2H)‐ones Using Sodium Borohydride in Water. Issue 16 (17th March 2020)

• Record Type: Journal Article
• Authors: Mondal, Amit; Singh, Shailesh Kumar; Saha, Nirmal; Husain, Syed Masood
• Other Names: Aggarwal Varinder K. guestEditor.
• Is Part Of: European journal of organic chemistry. Issue 16(2020)
• Page Start: 2425
• Page End: 2430
• Publication Date: 2020-03-17
• Subjects: Dihydroanthracenones -- Biomimetic synthesis -- Sodium borohydride -- Enantioselectivity -- Bisanthraquinones; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000096
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Herein, we report a single step synthesis of racemic dihydroanthracenones by the reduction of anthraquinones using NaBH4 and Na2 S2 O4 in water. The racemic mixture is utilized to determine the enantiomeric excess for the chiral dihydroanthracenones reportedly synthesized by the chemoenzymatic reduction of anthraquinones. The results show > 99% ee for the putative biosynthetic intermediates, ( R )‐configured dihydroanthracenones obtained through chemoenzymatic reduction of emodin, lunatin, and citreorosein using MdpC of Aspergillus nidulans or PHAR of Cochliobolus lunatus . This also implied for the confirmation about the optical purity of the natural products which are synthesized using chiral dihydroanthracenones. Abstract : We report a first synthesis of racemic dihydroanthracenones through regioselective reduction of hydroanthraquinones using NaBH4 in water. Their use confirms the enantiopurity of chiral dihydroanthracenones synthesized chemoenzymatically and of the bisanthraquinone analogues.