Concise Synthesis of the Tricyclic Core of Platencin

• Published in: Angewandte Chemie (International ed.) Vol. 47; no. 33; pp. 6201 - 6203
• Main Authors: Yun, Sang Young, Zheng, Jun-Cheng, Lee, Daesung
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley-VCH Verlag 04.08.2008; WILEY-VCH Verlag; WILEY‐VCH Verlag; Wiley
• Subjects: Aminophenols - chemical synthesis; Aminophenols - chemistry; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; antibiotics; Chemistry; Chemistry, Multidisciplinary; Cyclization; natural products; Physical Sciences; Polycyclic Compounds - chemical synthesis; Polycyclic Compounds - chemistry; radical cyclization; ring-closing metathesis; Science & Technology; Streptomyces - metabolism; total synthesis; radical cyclization; FORMAL SYNTHESIS; ANTIBIOTIC PROPERTIES; OLEFIN METATHESIS; PLATENSIMYCIN; ring-closing metathesis; DISCOVERY; (+/-)-PLATENSIMYCIN; natural products; OXATETRACYCLIC CORE; ENANTIOSELECTIVE ROUTE; total synthesis; INHIBITOR; antibiotics; FABF
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.200801587

A radical change: Implementation of a radical‐mediated rearrangement of the bicyclo[3.2.1]octyl moiety to the bicyclo[2.2.2]octane structure has enabled a concise synthesis of the tricyclic core of platencin, a newly discovered antibiotic. An intramolecular aldol and a ring‐closing metathesis reaction were subsequently used to complete the synthesis of the tricycle (see scheme).