Asymmetric total synthesis of (+)-dragmacidin D reveals unexpected stereocomplexity.
The first asymmetric total synthesis of the bis-indole marine alkaloid (+)-dragmacidin D (1) has been achieved. This synthesis revises an earlier configurational assignment based on biosynthetic considerations and assigns an R absolute configuration to (+)-1. The current studies reveal that natural dragmacidin D is isolated as either a racemate or a scalemic mixture (39% ee).
†State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing 100191, China.
Fengying
F
Zhang
†State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing 100191, China.
Bin
B
Wang
§Institute for Molecular Bioscience, The University of Queensland, St. Lucia, Brisbane, QLD 4072, Australia.
Pritesh
P
Prasad
§Institute for Molecular Bioscience, The University of Queensland, St. Lucia, Brisbane, QLD 4072, Australia.
Robert J
RJ
Capon
†State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing 100191, China.|‡State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China.
Yanxing
Y
Jia
D000818:Animals; D002384:Catalysis; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008386:Marine Biology; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
D026121:Indole Alkaloids; C470335:dragmacidin D; D010165:Palladium