Bio-inspired formal total synthesis of (±)-bisabosqual A. Issue 4 (19th January 2023)

• Record Type: Journal Article
• Authors: Du, Xuanxuan; Liu, Hainan; Wu, Yumeng; Tang, Yu
• Is Part Of: Organic chemistry frontiers. Volume 10:Issue 4(2023)
• Page Start: 1042
• Page End: 1046
• Publication Date: 2023-01-19
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo01697d
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A new approach was developed to construct a hexahydrobenzofurobenzopyran ring system by an oxa -[3+3], Diels–Alder reaction and oxidative aromatization. As a synthetic application, the bio-inspired formal synthesis of bisabosqual A was achieved. Abstract : A new approach was developed to construct a hexahydrobenzofurobenzopyran ring system (6/6/5/6) by an oxa -[3 + 3] cycloaddition, intramolecular hetero-Diels–Alder reaction, oxidative aromatization, and oxidative cyclization cascade starting from 5-(hydroxymethyl)cyclohexane-1, 3-dione and (2 E, 6 E )-farnesal. This strategy provides a new solution for preparing tetracyclic hexahydrobenzofurobenzopyran rings with different functional groups at C-3′–C4′. As a synthetic application, the bio-inspired formal total synthesis of bisabosqual A was achieved.