title: Highly efficient and scalable synthesis of clionamine D.
abstract: Herein we describe an efficient and scalable synthesis of clionamine D (4), a special member with autophagy bioactivity and an unprecedented spirobislactone side chain in the novel aminosteroid clionamines. This synthesis features a quick access to α-methylene-γ-lactone 8 and a Mn(OAc)3-mediated radical [3 + 2] reaction to assemble the unique spirobislactone unit. Clionamine D (4) can also serve as a key synthetic precursor to other clionamine members.
authors.affiliation: The Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Sha-Sha
authors.initials: SS
authors.lastname: Wang
authors.forename: Yong
authors.initials: Y
authors.lastname: Shi
authors.forename: Wei-Sheng
authors.initials: WS
authors.lastname: Tian
mesh_terms: D000818:Animals; D007783:Lactones; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D007783:Lactones; D013141:Spiro Compounds; D013256:Steroids; C530919:clionamine D; C416683:methylene-lactone