SYNTHESIS OF SUNDIVERSIFOLIDE AND DIVERSIFOLIDE VIA A DIASTEREOSELECTIVE [3+2] NITRILE OXIDE CYCLOADDITION REACTION

被引：8

作者：

Sasaki, Hiroyuki ^{[1
]}

Yokoe, Hiromasa ^{[1
]}

Shindo, Mitsuru ^{[2
]}

Yoshida, Masahiro ^{[1
]}

Shishido, Kozo ^{[1
]}

机构：

[1] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan

[2] Kyushu Univ, Inst Mat Chem & Engn, Kasuga, Fukuoka 8168580, Japan

来源：

HETEROCYCLES | 2009年 / 77卷 / 02期

基金：

日本学术振兴会;

关键词：

Sesquiterpene; Diastereoselective Synthesis; 1,3-Dipolar Cycloaddition; Allelopathy; Kinetic Protonation; (+)-SUNDIVERSIFOLIDE; REDUCTION; SUBSTANCE;

D O I：

10.3987/COM-08-S(F)67

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective synthesis of the unnatural enantiomers (-)-sundiversifolide and (+)-diversifolide has been accomplished employing a diastereoselective intramolecular [3+2] nitrile oxide cycloaddition reaction as the key step.

引用

页码：773 / 777

页数：5

共 50 条

[31] Intramolecular [3+2] nitrone cycloaddition reaction: highly regio and diastereoselective synthesis of bicyclo[3.2.1]octane scaffolds
Bakthadoss, Manickam
Mushaf, Mohammad
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (47) : 9653 - 9659
[32] A theoretical investigation on the regioselectivity of the [3+2] cycloaddition of nitrile oxide and N-vinylpyrrole
Modanlou, Fariba
Hamzehloueian, Mahshid
STRUCTURAL CHEMISTRY, 2018, 29 (01) : 9 - 14
[33] Methylenecyclopentane annulation via formal [3+2] cycloaddition reaction
Takahashi, Y
Tanino, K
Kuwajima, I
TETRAHEDRON LETTERS, 1996, 37 (33) : 5943 - 5946
[34] A theoretical investigation on the regioselectivity of the [3+2] cycloaddition of nitrile oxide and N-vinylpyrrole
Fariba Modanlou
Mahshid Hamzehloueian
Structural Chemistry, 2018, 29 : 9 - 14
[35] An expedient diastereoselective synthesis of pyrrolidinyl spirooxindoles fused to sugar lactone via [3+2] cycloaddition of azomethine ylides
Rao, J. Naga Siva
Raghunathan, R.
TETRAHEDRON LETTERS, 2012, 53 (07) : 854 - 858
[36] Synthesis of 2-aryl-2H-tetrazoles via a regioselective [3+2] cycloaddition reaction
Patouret, Remi
Kamenecka, Theodore M.
TETRAHEDRON LETTERS, 2016, 57 (14) : 1597 - 1599
[37] Enantioselective Synthesis of Pyrroloindolines by a Formal [3+2] Cycloaddition Reaction
Repka, Lindsay M.
Ni, Jane
Reisman, Sarah E.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (41) : 14418 - 14420
[38] Enantioselective synthesis of pyrroloindoles by a formal [3+2] cycloaddition reaction
Repka, Lindsay M.
Ni, Jane
Reisman, Sarah E.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
[39] APPLICATION OF [3+2] NITRILE OXIDE CYCLOADDITION CHEMISTRY TO THE CONSTRUCTION OF RETINOID SKELETON AND TO A NEW FORMAL SYNTHESIS OF (+/-)-ASCOFURANONE AND GEIPARVARIN
BARALDI, PG
BIGONI, A
GUARNERI, M
MANFREDINI, S
POLLINI, GP
SIMONI, D
FARMACO, 1993, 48 (11): : 1515 - 1529
[40] Synthesis of Azaspiro[3.4]octanes via [3+2] Cycloaddition
Wang, Wen
Lu, Xiuhong
Dong, Xiaochun
Zhao, Weili
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (01) : 137 - 143

← 1 2 3 4 5 →