A Unified Strategy for the Synthesis of Natural Products Containing δ-Hydroxy-γ- Lactones through a Photoredox ATRA Reaction.

被引:3
作者
Fuentes-Pantoja, Francisco J. [1 ]
Cordero-Vargas, Alejandro [1 ]
机构
[1] Univ Nacl Autonoma Mexico, Inst Quim, Circuito Exterior S-N,Ciudad Univ, Mexico City 04510, DF, Mexico
关键词
Iodolactonization; Lactones; Natural Products; Photoredox; Total synthesis; STREPTOMYCES-GRISEOVIRIDIS FH-S-1832; METABOLITE PATTERN-ANALYSIS; ANGIOPTERLACTONE B; (-)-OSMUNDALACTONE; (-)-MURICATACIN; CINEROMYCINS; ANALOGS;
D O I
10.1002/ejoc.202200464
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A unified strategy for the synthesis of natural products containing delta-hydroxy-gamma-lactones as the main core is reported. This strategy is based on a photocatalyzed radical ionic sequence for the preparation of gamma-lactones. Depending on the necessities of the synthetic targets, the reaction conditions can be adjusted to access a diastereoisomeric mixture or a single diasteroisomer of the lactones. Also, delta-lactones can be prepared by this method. The utility of this procedure was demonstrated by the total synthesis of five natural products.
引用
收藏
页数:8
相关论文
共 31 条
  • [1] [Anonymous], 2015, ANGEW CHEM, V127, P8880
  • [2] Synthesis of (-)-(4R,5R)-muricatacin using a regio- and stereospecific ring-opening of a vinyl epoxide
    Baylon, C
    Prestat, G
    Heck, MP
    Mioskowski, C
    [J]. TETRAHEDRON LETTERS, 2000, 41 (20) : 3833 - 3835
  • [3] New cineromycins and musacins obtained by metabolite pattern analysis of Streptomyces griseoviridis (FH-S 1832) .1. Taxonomy, fermentation, isolation and biological activity
    Burkhardt, K
    Fiedler, HP
    Grabley, S
    Thiericke, R
    Zeeck, A
    [J]. JOURNAL OF ANTIBIOTICS, 1996, 49 (05) : 432 - 437
  • [4] Carda M, 2002, EUR J ORG CHEM, V2002, P2649
  • [5] STEREOSPECIFIC SYNTHESIS OF (+)-MURICATACIN - A BIOLOGICALLY-ACTIVE ACETOGENIN DERIVATIVE
    FIGADERE, B
    HARMANGE, JC
    LAURENS, A
    CAVE, A
    [J]. TETRAHEDRON LETTERS, 1991, 32 (51) : 7539 - 7542
  • [6] Total Synthesis of (R)-Argentilactone and (R)-Goniothalamin Using a Free-Radical Photoredox Approach to α,β-Unsaturated δ-Lactones
    Fuentes-Pantoja, Francisco J.
    Cordero-Vargas, Alejandro
    [J]. SYNTHESIS-STUTTGART, 2021, 53 (23): : 4433 - 4439
  • [7] Phytotoxicity of three lactones from Nigrospora sacchari
    Fukushima, T
    Tanaka, M
    Gohbara, M
    Fujimori, T
    [J]. PHYTOCHEMISTRY, 1998, 48 (04) : 625 - 630
  • [8] Probing the steric requirements of the γ-aminobutyric acid aminotransferase active site with fluorinated analogues of vigabatrin
    Juncosa, Jose I., Jr.
    Groves, Andrew P.
    Xia, Guoyao
    Silverman, Richard B.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (04) : 903 - 911
  • [9] Formal Synthesis of Angiopterlactone B via Enantioselective Reduction of Ketone with Daucus Carota Root
    Khomane, Navnath B.
    Patel, Javed S.
    Shirsat, Prashishkumar K.
    Mali, Prakash R.
    Meshram, Harshadas M.
    [J]. CHEMISTRYSELECT, 2018, 3 (05): : 1517 - 1520
  • [10] Biomimetic Total Synthesis of Angiopterlactone B and Other Potential Natural Products
    Kotammagari, Tharun K.
    Gonnade, Rajesh G.
    Bhattacharya, Asish K.
    [J]. ORGANIC LETTERS, 2017, 19 (13) : 3564 - 3567