title: Krishnadimer A, an Axially Chiral Non-biaryl Natural Product: Discovery and Biomimetic Synthesis.
abstract: Krishnadimer A (1a), a C2-symmetric limonoid dimer representing a new class of axially chiral nonbiaryl natural products, was isolated and biomimetically semisynthesized by atroposelective 2,3-dichloro-5,6-dicyanobenzoquinone-mediated dienol-oxidative coupling. Single-crystal X-ray diffraction and electronic circular dichroism spectral analysis on the synthesized 1a unambiguously established its absolute configuration, including the P-configuration of the C15-C15' central axis. Antitumor investigations of the synthesized dimers 1a, 2a, and 2b revealed the large impact of axial chirality on bioactivities.
authors.affiliation: Marine Drugs Research Center, College of Pharmacy, Jinan University , 601 Huangpu Avenue West, Guangzhou 510632, P. R. China.
authors.forename: Wan Shan
authors.initials: WS
authors.lastname: Li
authors.affiliation: Marine Drugs Research Center, College of Pharmacy, Jinan University , 601 Huangpu Avenue West, Guangzhou 510632, P. R. China.
authors.forename: Jun
authors.initials: J
authors.lastname: Wu
authors.affiliation: Institute of Organic Chemistry, University of Würzburg , Am Hubland, Würzburg D-97074, Germany.
authors.forename: Jun
authors.initials: J
authors.lastname: Li
authors.affiliation: Government Degree College at Amadala valasa , Srikakulam District, Andhra Pradesh 532185, India.
authors.forename: Tirumani
authors.initials: T
authors.lastname: Satyanandamurty
authors.affiliation: Marine Drugs Research Center, College of Pharmacy, Jinan University , 601 Huangpu Avenue West, Guangzhou 510632, P. R. China.
authors.forename: Li
authors.identifier: 0000-0001-5770-1607
authors.initials: L
authors.lastname: Shen
authors.affiliation: Institute of Organic Chemistry, University of Würzburg , Am Hubland, Würzburg D-97074, Germany.
authors.forename: Gerhard
authors.identifier: 0000-0002-3583-5935
authors.initials: G
authors.lastname: Bringmann
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000302:isolation & purification / Q000494:pharmacology; D016227:Benzoquinones / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000302:isolation & purification*; D032701:Biomimetics; D045744:Cell Line, Tumor; D019281:Dimerization; D055808:Drug Discovery; D006801:Humans; D036701:Limonins / Q000138:chemical synthesis* / Q000302:isolation & purification* / Q000494:pharmacology; D058451:Oxidative Coupling; D013237:Stereoisomerism; D064028:Tracheophyta / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D016227:Benzoquinones; D001688:Biological Products; D036701:Limonins; C004532:quinone