SYNTHESIS OF 6Z-PANDANAMINE BY REGIOSELECTIVE CYCLIZATION REACTION OF 2-EN-4-YNOIC ACID DERIVATIVES PROMOTED BY WEAK BASE

被引：2
|
作者：
Hiroya, Kou [1 ,2 ]
Takuma, Kazuya [1 ]
Inamoto, Kiyofumi [1 ]
Sakamoto, Takao [1 ,2 ]
机构：
[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan
[2] Tohoku Univ, 21st Century COE Program, Comprehens Res & Educ Ctr Planning Drug Dev & Cli, Sendai, Miyagi 9808578, Japan
来源：
HETEROCYCLES | 2009年 / 77卷 / 01期
基金：
日本学术振兴会;
关键词：
Cyclization Reaction; 6Z-Pandanamine; 2-En-4-yne-carboxylic Acid; Base; O-IODOBENZOIC ACID; PANDANUS-AMARYLLIFOLIUS; PANDAMARILACTONINE-A; INTRAMOLECULAR CYCLIZATION; GRIGNARD-REAGENTS; ALKALOIDS; HYDROAMINATION; HETEROCYCLES; ISOCOUMARINS; PHTHALIDES;
D O I：
10.3987/COM-08-S(F)48
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The stereoselective synthesis of 6Z-pandanamine by base-promoted 5-exo-dig-selective cyclization reaction of bis-2-en-4-ynoic acid derivative as a key step is described
引用
收藏
页码：493 / 505
页数：13
相关论文
共 50 条
  • [1] SYNTHESIS AND REACTIVITY OF 6-SUBSTITUTED (Z)-2-EN-4-YNOIC ACIDS
    STRUVE, G
    SELTZER, S
    JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (11): : 2109 - 2113
  • [2] SYNTHESIS OF 4-YLIDENEBUTENOLIDES - A PRACTICAL ROUTE TO 2-EN-4-YNOIC ACID INTERMEDIATES BASED ON CONJUGATE ADDITION OF ALKYNYL-LITHIUM REAGENTS
    CLEMO, NG
    PATTENDEN, G
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (12): : 2133 - 2136
  • [3] A CONVENIENT STEREOSELECTIVE SYNTHESIS OF CONJUGATED (2Z)-EN-4-YNOIC AND (2Z,4Z)-DIENOIC AND (2Z,4E)-DIENOIC ACID-DERIVATIVES FROM PROPIOLIC ACID-DERIVATIVES
    LU, XY
    HUANG, XL
    MA, SM
    TETRAHEDRON LETTERS, 1992, 33 (18) : 2535 - 2538
  • [4] Selective synthesis of natural and unnatural 5,6-disubstituted 2(2H)-pyranones via iodolactonization of 5-substituted (Z)-2-en-4-ynoic acids
    Bellina, F
    Biagetti, M
    Carpita, A
    Rossi, R
    TETRAHEDRON, 2001, 57 (14) : 2857 - 2870
  • [5] Efficient Synthesis of Polysubstituted Furans through a Base-Promoted Oxacyclization of (Z)-2-En-4-yn-1-ols
    Hrizi, Asma
    Thiery, Emilie
    Romdhani-Younes, Moufida
    Jacquemin, Johan
    Thibonnet, Jerome
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (27) : 3798 - 3806
  • [6] Highly efficient and selective procedures for the synthesis of gamma-alkylidenebutenolides via palladium-catalyzed ene-yne coupling and palladium- or silver-catalyzed lactonization of (Z)-2-en-4-ynoic acids. Synthesis of rubrolides A, C, D, and E
    Kotora, M
    Negishi, E
    SYNTHESIS-STUTTGART, 1997, (01): : 121 - &
  • [7] Regioselective base-promoted nucleophilic ring opening of spirocyclic 2,6-dioxopiperazines:: Synthesis of N-(1-carboxycyclohexyl)amino acid derivatives
    Gonzalez-Vera, Juan A.
    Garcia-Lopez, M. Teresa
    Herranz, Rosario
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (03) : 548 - 554
  • [8] Synthesis of chiral 4-substituted 2-hydroxypent-4-enoic acid derivatives via diastereoselective ene reaction promoted by ZnBr2
    Kwiatkowski, Piotr
    Kwiatkowski, Jacek
    Majer, Jakub
    Jurczak, Janusz
    TETRAHEDRON-ASYMMETRY, 2007, 18 (02) : 215 - 223
  • [9] Synthesis of 4-arylaminoquinazoline-2-carboxylic acid derivatives by the reaction of (Z)-2-amino-N′-arylbenzimidamides with some selected anhydrides
    El-Shaieb, Kamal M.
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2019, 74 (7-8): : 603 - 606
  • [10] Synthesis of 1,2,4-diazaphospholes via base-promoted cyclization reaction of hydrazonoyl chlorides and [Bu4N][P(SiCl3)2]
    Wang, Xin
    Luo, Hui
    Yang, Bo
    Li, Ming
    Ma, Yong-Jun
    Wang, Xi-Cun
    Quan, Zheng-Jun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (35) : 7138 - 7142
12345