Alkynyliodonium salts in organic synthesis. Application to the total synthesis of (-)-agelastatin A and (-)-agelastatin B

被引：75
|
作者：
Feldman, KS [1 ]
Saunders, JC [1 ]
机构：
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 31期
关键词：
D O I：
10.1021/ja027121e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The asymmetric total syntheses of (-)-agelastatin A and (-)-agelastatin B were accomplished in 14 steps each from (R)-epichlorohydrin. The pivotal transformation in both sequences was a sulfinate-promoted cyclization of an alkynyliodonium salt to furnish a key functionalized cyclopentene intermediate. Selective bromination in the final step led to either agelastatin A or agelastatin B, depending upon conditions. Copyright © 2002 American Chemical Society.
引用
收藏
页码：9060 / 9061
页数：2
相关论文
共 50 条
  • [1] Alkynyliodonium salts in organic synthesis. Application to the total synthesis of (-)-Agelastatin A and (-)-Agelastatin B
    Feldman, Ken S.
    Saunders, Joe C.
    1600, American Chemical Society (124):
  • [2] Alkynyliodonium salts in organic synthesis. Development of a unified strategy for the syntheses of (-)-agelastatin A and (-)-agelastatin B
    Feldman, KS
    Saunders, JC
    Wrobleski, ML
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20): : 7096 - 7109
  • [3] Total Synthesis of (-)-Agelastatin A
    Yoshimitsu, Takehiko
    Ino, Tatsunori
    Tanaka, Tetsuaki
    ORGANIC LETTERS, 2008, 10 (23) : 5457 - 5460
  • [4] Alkynyliodonium salts in organic synthesis. Application to the total synthesis of the tropoloisoquinoline alkaloid pareitropone
    Feldman, KS
    Cutarelli, TD
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) : 11600 - 11601
  • [5] Total Synthesis of (-)-Agelastatin A: The Application of a Sequential Sigmatropic Rearrangement
    Hama, Naoto
    Matsuda, Tomoki
    Sato, Takaaki
    Chida, Noritaka
    ORGANIC LETTERS, 2009, 11 (12) : 2687 - 2690
  • [6] Bioinspired Total Synthesis of Agelastatin A
    Reyes, Jeremy Chris P.
    Romo, Daniel
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (28) : 6870 - 6873
  • [7] Bioinspired total synthesis of Agelastatin A
    Reyes, Jeremy Chris P.
    Romo, Daniel
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [8] Total synthesis of all (-)-agelastatin alkaloids
    Movassaghi, Mohammad
    Siegel, Dustin S.
    Han, Sunkyu
    CHEMICAL SCIENCE, 2010, 1 (05) : 561 - 566
  • [9] Approaches to total synthesis of agelastatin A.
    Stein, D
    Anderson, GT
    Chase, CE
    Koh, YH
    Weinreb, SM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U217 - U217
  • [10] Studies toward the total synthesis of agelastatin A
    Morrow, Matthew
    Gholami, Hadi
    Borhan, Babak
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
12345