title: Synthesis study on marmycin A: preparation of the C3'-desmethyl analogues.
abstract: Total synthesis of natural product marmycin A was studied. An expeditious synthetic strategy for the key fragment 8-amino-3-methylbenz[a]anthraquinone (1) was established with decarboxylative alkylation, Pd(OAc)(2)-catalyzed cyclization, aromatization, and C-N coupling as the key steps. However, final assembly of marmycin A was hampered by the failure to obtain the carbohydrate fragment 2. Instead, a small library of desmethyl analogues of marmycin A was prepared in moderate yields by using the InBr(3)-catalyzed C- and N-glycosidation reaction. The absolute configuration of these compounds was confirmed by comparison of their spectroscopic data with that reported for marmycin A, and by X-ray analysis.
authors.affiliation: Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing, China 210009.
authors.forename: Chunyong
authors.initials: C
authors.lastname: Ding
authors.forename: Shanghui
authors.initials: S
authors.lastname: Tu
authors.forename: Fuying
authors.initials: F
authors.lastname: Li
authors.forename: Yuanxiang
authors.initials: Y
authors.lastname: Wang
authors.forename: Qizheng
authors.initials: Q
authors.lastname: Yao
authors.forename: Wenxiang
authors.initials: W
authors.lastname: Hu
authors.forename: Hua
authors.initials: H
authors.lastname: Xie
authors.forename: Linghua
authors.initials: L
authors.lastname: Meng
authors.forename: Ao
authors.initials: A
authors.lastname: Zhang
mesh_terms: D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000880:Anthraquinones; D000970:Antineoplastic Agents; C524224:marmycin A