title: A concise formal synthesis of (-)-hamigeran B.
abstract: A concise and efficient formal synthesis of (-)-hamigeran B is reported. The critical intermediate was synthesized from 3-methoxy-5-methylphenyl trifluoromethanesulfonate with an 11-steps 7.2% total yield route. The chiral quaternary carbon was efficiently and steroselectively constructed through an intermolecular Pauson-Khand reaction and a Claisen rearrangement reaction with >99% ee; the cyclohexane B was then closed through an aldehyde Friedel-Crafts cyclization. Lastly, the isopropenyl group of ring C was introduced through a Suzuki coupling reaction.
authors: CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China. jiangb@sioc.ac.cn
authors: Biao
authors: B
authors: Jiang
authors: Ming-Ming
authors: MM
authors: Li
authors: Ping
authors: P
authors: Xing
authors: Zuo-Gang
authors: ZG
authors: Huang
mesh_terms: D000818:Animals; D003500:Cyclization; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D009285:Naphthoquinones; C483756:hamigeran B