Studies on the total synthesis of streptazolin and its related natural products:: First total synthesis of (±)-8α-hydroxystreptazolone

被引：38

作者：

Nomura, I ^{[1
]}

Mukai, C ^{[1
]}

机构：

[1] Kanazawa Univ, Fac Pharmaceut Sci, Kanazawa, Ishikawa 9200934, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 06期

关键词：

D O I：

10.1021/jo0356816

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intramolecular Pauson-Khand reaction of 2-oxazolone derivatives with a suitable heptynyl appendage gave exclusively the corresponding 4-hydroxy-6-substituted-9-oxa-1-azatricyclo[6.2.1.0(5,11)]undec-5-ene-7,10-diones. On the basis of this newly developed Pauson-Khand reaction of 2-oxazolone-alkyne derivatives, the first total synthesis of (+/-)-8alpha-hydroxystreptazolone was accomplished in a highly stereoselective manner. In addition, (+/-)-7-epi-8alpha-hydroxystreptazolone was also synthesized.

引用

页码：1803 / 1812

页数：10

共 50 条

[31] Total synthesis of polyyne natural products
Gung, Benjamin W.
COMPTES RENDUS CHIMIE, 2009, 12 (3-4) : 489 - 505
[32] Total synthesis of natural products.
Joullié, MM
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U169 - U169
[33] Biosynthesis and Total Synthesis Studies on the Jadomycin Family of Natural Products
Sharif, Ehesan U.
O'Doherty, George A.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (11) : 2095 - 2108
[34] Chemoenzymatic Total Synthesis of Natural Products
Chakrabarty, Suman
Romero, Evan O.
Pyser, Joshua B.
Yazarians, Jessica A.
Narayan, Alison R. H.
ACCOUNTS OF CHEMICAL RESEARCH, 2021, 54 (06) : 1374 - 1384
[35] Total synthesis of grayanane natural products
Fay, Nicolas
Blieck, Remi
Kouklovsky, Cyrille
de la Torre, Aurelien
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2022, 18 : 1707 - 1719
[36] Total Synthesis of Fused Natural Products
Ohyoshi, Takayuki
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2024, 82 (12) : 1184 - 1194
[37] THE TOTAL SYNTHESIS OF NATURAL-PRODUCTS
IRELAND, RE
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 195 : 74 - ORGN
[38] Fluorescent total synthesis of natural products
La Clair, James J.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3017 - U3018
[39] Birch reduction and its application in the total synthesis of natural products
Rao, GSRS
PURE AND APPLIED CHEMISTRY, 2003, 75 (10) : 1443 - 1451
[40] The first total synthesis of natural (-)-tetracycline
Tatsuta, K
Yoshimoto, T
Gunji, H
Okado, Y
Takahashi, M
CHEMISTRY LETTERS, 2000, (06) : 646 - 647

← 1 2 3 4 5 →