Stereocontrolled Synthesis as an Enabling Tool for the Configurational Assignment of Marine Polyketide Natural Products

被引：14
|
作者：
Lam, Nelson Y. S. [1 ]
Paterson, Ian [1 ]
机构：
[1] Univ Chem Lab, Lensfield Rd, Cambridge CB2 1EW, England
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 16期
关键词：
Aldol reactions; Natural products; Polyketides; Stereocontrol; Total synthesis; MICROTUBULE-STABILIZING MACROLIDE; STEREOCHEMICAL DETERMINATION; RELATIVE CONFIGURATION; STRUCTURAL ELUCIDATION; ALDOL CONDENSATIONS; CALLIPELTOSIDE-A; DRUG DISCOVERY; POWERFUL TOOL; ABSOLUTE; DICTYOSTATIN;
D O I：
10.1002/ejoc.201901243
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Marine polyketide natural products represent a fertile area of chemical space for the continual discovery of promising drug candidates. Advancements in spectroscopic and computational techniques have allowed for the increasingly facile structural and stereochemical determination of these biologically active molecules. However, their inherent architectural complexity often precludes a complete assignment even by the most discerning isolation chemists. This Minireview highlights how carefully conceived synthetic plans, employing highly stereocontrolled reactions, have enabled the configurational assignment of several polyketide natural products.
引用
收藏
页码：2310 / 2320
页数：11
相关论文
共 50 条
  • [1] Integrated approaches to the configurational assignment of marine natural products
    Molinski, Tadeusz F.
    Morinaka, Brandon I.
    [J]. TETRAHEDRON, 2012, 68 (46) : 9307 - 9343
  • [2] Total Synthesis and Configurational Assignment of the Marine Natural Product Haliclamide
    Pfeiffer, Bernhard
    Speck-Gisler, Sandra
    Barandun, Luzi
    Senft, Ursula
    de Groot, Claire
    Lehmann, Irene
    Ganci, Walter
    Gertsch, Juerg
    Altmann, Karl-Heinz
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (06): : 2553 - 2563
  • [3] The Stereocontrolled Total Synthesis of Polyketide Natural Products: A Thirty-Year Journey
    Stockdale, Tegan P.
    Lam, Nelson Y. S.
    Anketell, Matthew J.
    Paterson, Ian
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2021, 94 (02) : 713 - 731
  • [4] STEREOCONTROLLED SYNTHESIS OF CHIRAL SYNTHONS FOR POLYKETIDE-DERIVED NATURAL-PRODUCTS
    OIKAWA, Y
    NISHI, T
    ITAYA, H
    YONEMITSU, O
    [J]. TETRAHEDRON LETTERS, 1983, 24 (19) : 1987 - 1990
  • [5] Anodic Oxidation as an Enabling Tool for the Synthesis of Natural Products
    Geske, Leander
    Sato, Eisuke
    Opatz, Till
    [J]. SYNTHESIS-STUTTGART, 2020, 52 (19): : 2781 - 2794
  • [6] Configurational Assignment of Secondary Hydroxyl Groups and Methyl Branches in Polyketide Natural Products through Bioinformatic Analysis of the Ketoreductase Domain
    Kitsche, Andreas
    Kalesse, Markus
    [J]. CHEMBIOCHEM, 2013, 14 (07) : 851 - 861
  • [7] STEREOCONTROLLED SYNTHESIS OF MARINE CYTOTOXIC NATURAL PRODUCT
    ICHIKAWA, Y
    [J]. NIPPON NOGEIKAGAKU KAISHI-JOURNAL OF THE JAPAN SOCIETY FOR BIOSCIENCE BIOTECHNOLOGY AND AGROCHEMISTRY, 1991, 65 (11): : 1627 - 1634
  • [8] SYNTHESIS OF THE ENANTIOMERS OF UMBELACTONE - CONFIGURATIONAL ASSIGNMENT OF THE NATURAL PRODUCT
    ORTUNO, RM
    BIGORRA, J
    FONT, J
    [J]. TETRAHEDRON, 1987, 43 (09) : 2199 - 2202
  • [9] Synthesis-Driven Stereochemical Assignment of Marine Polycyclic Ether Natural Products
    Fuwa, Haruhiko
    [J]. MARINE DRUGS, 2021, 19 (05)
  • [10] Stereocontrolled Total Synthesis of Biologically Active Natural Products
    Hatakeyama, Susumi
    [J]. YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 2018, 138 (02): : 191 - 209
12345