Synthesis study on marmycin A: preparation of the C3'-desmethyl analogues.
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.
Ding
Chunyong
C
Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing, China 210009.
Tu
Shanghui
S
Li
Fuying
F
Wang
Yuanxiang
Y
Yao
Qizheng
Q
Hu
Wenxiang
W
Xie
Hua
H
Meng
Linghua
L
Zhang
Ao
A
D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry*
D000880:Anthraquinones; D000970:Antineoplastic Agents; C524224:marmycin A