Total synthesis and preliminary SAR study of (±)-merochlorins A and B. Issue 1 (26th October 2015)

• Record Type: Journal Article
• Authors: Yang, Hongzhi; Liu, Xue; Li, Qingong; Li, Longbo; Zhang, Jing-Ren; Tang, Yefeng
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 1(2016)
• Page Start: 198
• Page End: 205
• Publication Date: 2015-10-26
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob01946j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A modular synthesis of merochlorins A and B, two naturally occurring antibiotics, has been achieved from the readily available building blocks in a highly concise manner. Abstract : A modular synthesis of merochlorins A and B, two naturally occurring antibiotics, has been achieved concisely from readily available building blocks in 4–6 steps. The key steps include the bio-inspired tandem phenol oxidative dearomatization/[5 + 2] and [3 + 2] cycloadditions to construct the tricyclic cores of the targets, and the intermolecular Diels–Alder reaction followed by dehydrogenative aromatization to assemble the remaining aromatic units. The antibacterial activities of merochlorins A, B and some advanced synthetic intermediates were also evaluated, which provided valuable information on the structure–activity relationship (SAR) of this class of new antibiotics.