Stereoselective Synthesis of Highly Substituted O-Heterocycles via Matteson Homologation: A Ring-Closing Metathesis Approach

被引:2
作者
Kinsinger, Thorsten [1 ]
Schaefer, Patrick [1 ]
Kazmaier, Uli [1 ]
机构
[1] Saarland Univ, Organ Chem 1, D-66123 Saarbrucken, Germany
关键词
PROTECTED SIDE-CHAIN; BORONIC ESTERS; NATURAL-PRODUCTS; RUCL2(=CHR)(PR(3))(2); DERIVATIVES; COMPLEXES; MACROLIDE; CATALYSTS;
D O I
10.1021/acs.orglett.3c01099
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Matteson homologations of chiral boronic esters with the aid of unsaturated nucleophiles are powerful for gaining access to a range of different O-heterocycles via subsequent ring-closing metatheses. Using this protocol, six-to eight-membered rings become available and almost any position of the ring can be substituted and/or functionalized.
引用
收藏
页码:3303 / 3307
页数:5
相关论文
共 50 条
  • [41] Synthesis of the Spirofungin A Core via a Domino Strategy Consisting of Olefinic Ester Ring-Closing Metathesis and Iodospiroacetalization
    Neumaier, Jochen
    Maier, Martin E.
    SYNLETT, 2011, (02) : 187 - 190
  • [42] Stereoselective synthesis of exocyclic alkenes by Cu-catalyzed allylmagnesiation, Pd-catalyzed alkylation, and Ru-catalyzed ring-closing metathesis:: Highly stereoselective synthesis of (Z)- and (E)-γ-bisabolenes
    Anastasia, L
    Dumond, YR
    Negishi, E
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (16) : 3039 - 3043
  • [43] Synthesis of medium-sized aryl-fused nitrogenous heterocycles via sequential aryne aza-Claisen rearrangement/ring-closing metathesis
    Mangina, N. S. V. M. Rao
    Guduru, Ravinder
    Karunakar, Galla V.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (12) : 2134 - 2142
  • [44] Medium-Ring Stereocontrol in the Temporary Silicon-Tethered Ring-Closing Metathesis Approach to the Synthesis of Polyketide Fragments
    Evans, P. Andrew
    Cusak, Alen
    Grisin, Aleksandr
    Lawler, Michael J.
    Pink, Maren
    SYNTHESIS-STUTTGART, 2016, 48 (15): : 2402 - 2412
  • [45] Synthesis of Heterocycles through a Ruthenium-Catalyzed Tandem Ring-Closing Metathesis/Isomerization/N-Acyliminium Cyclization Sequence
    Ascic, Erhad
    Jensen, Jakob F.
    Nielsen, Thomas E.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (22) : 5188 - 5191
  • [46] Synthetic Approach to the ABCD Ring System of Anticancer Agent Fredericamycin A via Claisen Rearrangement and Ring-Closing Metathesis as Key Steps
    Kotha, Sambasivarao
    Cheekatla, Subba Rao
    Fatma, Ambareen
    ACS OMEGA, 2019, 4 (17): : 17109 - 17116
  • [47] A Concise Formal Total Synthesis of (±)-Centrolobine via DDQ-Mediated Diastereoselective Allylation and Ring-Closing Metathesis
    Kim, Hyoungsu
    Lee, Dongjoo
    SYNLETT, 2015, 26 (18) : 2583 - 2587
  • [48] Synthesis of N-Sulfonyl- and N-Acylpyrroles via a Ring-Closing Metathesis/Dehydrogenation Tandem Reaction
    Chen, Weiqiang
    Zhang, Yin-Lin
    Li, Hui-Jing
    Nan, Xiang
    Liu, Ying
    Wu, Yan-Chao
    SYNTHESIS-STUTTGART, 2019, 51 (19): : 3651 - 3666
  • [49] Synthesis of Dihydropyrano[3,2-c]pyrazoles via Double Bond Migration and Ring-Closing Metathesis
    Usami, Yoshihide
    Sumimoto, Kodai
    Kishima, Azusa
    Tatsui, Yuya
    Yoneyama, Hiroki
    Harusawa, Shinya
    MOLECULES, 2019, 24 (02)
  • [50] Diversity-Oriented Synthesis of 13- to 18-Membered Macrolactams via Ring-Closing Metathesis
    Dandapani, Sivaraman
    Lowe, Jason T.
    Comer, Eamon
    Marcaurelle, Lisa A.
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (19) : 8042 - 8048