Total synthesis of (-)-agelastatin A: an SH2′ radical azidation strategy

被引：14

作者：

Tsuchimochi, Izuru ^{[1
,2
]}

Kitamura, Yuta ^{[2
]}

Aoyama, Hiroshi ^{[2
]}

Akai, Shuji ^{[2
]}

Nakai, Keiyo ^{[1
]}

Yoshimitsu, Takehiko ^{[1
]}

机构：

[1] Okayama Univ, Div Pharmaceut Sci, Grad Sch Med Dent & Pharmaceut Sci, Kita Ku, 1-1-1 Tsushima Naka, Okayama 7008530, Japan

[2] Osaka Univ, Grad Sch Pharmaceut Sci, 1-6 Yamadaoka, Suita, Osaka 5650871, Japan

来源：

CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 71期

关键词：

SPONGE AGELAS-DENDROMORPHA; ABSOLUTE-CONFIGURATION; ALKYNYLIODONIUM SALTS; FACILE ISOMERIZATION; ORGANIC-SYNTHESIS; FORMAL SYNTHESIS; ENOL ETHERS; CORAL SEA; INHIBITION; GSK-3-BETA;

D O I：

10.1039/c8cc05697h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A reagent generated from TMSN3/KMnO4/BnEt3NCl was found to promote an S(H)2' radical azidation of a bromo silyl enol ether to furnish an azido silyl enol ether via olefin transposition. With the present azidation protocol, a new synthetic approach to agelastatin A, a potent antitumor marine alkaloid, has been established.

引用

页码：9893 / 9896

页数：5

共 50 条

[1] RADICAL REACTIONS IN SYNTHESIS - INTRAMOLECULAR SH2' MACROCYCLISATIONS
BALDWIN, JE
ADLINGTON, RM
MITCHELL, MB
ROBERTSON, J
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (22) : 1574 - 1575
[2] Total Synthesis of (-)-Agelastatin A
Yoshimitsu, Takehiko
Ino, Tatsunori
Tanaka, Tetsuaki
ORGANIC LETTERS, 2008, 10 (23) : 5457 - 5460
[3] Free radical SH2′ reaction mechanism study by comparing free radical SH2′ reaction with free radical addition reaction
Wu, Yuh-Wern
Huang, Hsu-Ting
Chen, YiJing
Yang, Jyh-Ferng
TETRAHEDRON, 2006, 62 (25) : 6061 - 6064
[4] "Bio-inspired" strategy toward the total synthesis of agelastatin A
Reyes, Jeremy Chris P.
Watson, Lucas W.
Romo, Daniel
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
[5] Bioinspired Total Synthesis of Agelastatin A
Reyes, Jeremy Chris P.
Romo, Daniel
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (28) : 6870 - 6873
[6] Bioinspired total synthesis of Agelastatin A
Reyes, Jeremy Chris P.
Romo, Daniel
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
[7] Total synthesis of all (-)-agelastatin alkaloids
Movassaghi, Mohammad
Siegel, Dustin S.
Han, Sunkyu
CHEMICAL SCIENCE, 2010, 1 (05) : 561 - 566
[8] 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
[9] Alkynyliodonium salts in organic synthesis. Application to the total synthesis of (-)-agelastatin A and (-)-agelastatin B
Feldman, KS
Saunders, JC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (31) : 9060 - 9061
[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

← 1 2 3 4 5 →