Applications of sharpless asymmetric dihydroxylation in the total synthesis of natural products

被引：64

作者：

Heravi, Majid M. ^{[1
]}

Zadsirjan, Vahideh ^{[1
]}

Esfandyari, Maryam ^{[1
]}

Lashaki, Tahmineh Baie ^{[1
]}

机构：

[1] Alzahra Univ, Sch Sci, Dept Chem, Tehran, Iran

来源：

TETRAHEDRON-ASYMMETRY | 2017年 / 28卷 / 08期

基金：

美国国家科学基金会;

关键词：

STEREOSELECTIVE TOTAL-SYNTHESIS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; SPIRASTRELLOLIDE-A CONSTRUCTION; EFFICIENT TOTAL-SYNTHESIS; PLANT ANTITUMOR AGENTS; WATER MARINE SPONGE; ALPHA-LIPOIC ACID; ANNONACEOUS ACETOGENINS; KINETIC RESOLUTION; STRUCTURE ELUCIDATION;

D O I：

10.1016/j.tetasy.2017.07.004

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Sharpless asymmetric dihydroxylation involves the reaction of an alkene with osmium tetroxide in the presence of a chiral quinine ligand to form an optically active vicinal diol. This reaction was primarily developed by Sharpless based on the already known racemic Upjohn dihydroxylation. The chiral diols obtained by Sharpless asymmetric dihydroxylation are important intermediates in organic synthesis. Herein, we emphasise the applications of Sharpless asymmetric dihydroxylation in the total synthesis of natural products. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：987 / 1043

页数：57

共 50 条

[31] Asymmetric total synthesis of complex marine natural products
Hassfeld, J
Kalesse, M
Stellfeld, T
Christmann, M
MARINE BIOTECHNOLOGY II, 2005, 97 : 133 - 203
[32] An investigative study of kinetic resolutions by the Sharpless asymmetric dihydroxylation reaction
Hamon, DPG
Tuck, KL
Christie, HS
TETRAHEDRON, 2001, 57 (46) : 9499 - 9508
[33] Application of sharpless dihydroxylation: Asymmetric synthesis of sulfur and oxygen containing novel amino acids.
Xiong, CY
Wang, W
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 223 : B188 - B189
[34] Enantioselective synthesis of various hexoses via the sharpless catalytic asymmetric dihydroxylation reaction of vinylfuran.
O'Doherty, GA
Keranen, MD
Harris, JM
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 215 : U101 - U101
[35] Enantioselective synthesis of various hexoses via the sharpless catalytic asymmetric dihydroxylation reaction of vinylfuran.
Keranen, MD
Harris, JM
O'Doherty, GA
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 215 : U285 - U285
[36] Asymmetric total synthesis of (+)-cardiobutanolide via an iterative asymmetric dihydroxylation in PEG
Chandrasekhar, S.
Kiranmai, N.
TETRAHEDRON LETTERS, 2010, 51 (31) : 4058 - 4060
[37] Synthesis and catalytic activity of tentagel-supported Sharpless's asymmetric dihydroxylation ligand.
Fenniri, H
Hunt, JR
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U229 - U229
[38] CATALYTIC ENANTIOSELECTIVE SYNTHESIS OF 20(S)-CAMPTOTHECIN - A PRACTICAL APPLICATION OF THE SHARPLESS ASYMMETRIC DIHYDROXYLATION REACTION
FANG, FG
XIE, SP
LOWERY, MW
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21): : 6142 - 6143
[39] AN ACCESS TO ERYTHRO-DIOLS VIA SHARPLESS ASYMMETRIC DIHYDROXYLATION REACTION
KO, SY
MALIK, M
DICKINSON, AF
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09): : 2570 - 2576
[40] KINETIC RESOLUTION OF MONOCYCLIC AND BICYCLIC OLEFINS VIA SHARPLESS ASYMMETRIC DIHYDROXYLATION
BAKKEREN, FJAD
KLUNDER, AJH
ZWANENBURG, B
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 438 - ORGN

← 1 2 3 4 5 →