Manganese(III)-Promoted Tandem Oxidation and Cyclization of β-Keto Ester Derivatives of Terpenoids

被引：18

作者：

Li, Zhilong ^{[1
,2
]}

Jung, Heejung ^{[2
]}

Park, Mira ^{[3
]}

Lah, Myoung Soo ^{[4
]}

Koo, Sangho ^{[1
,2
]}

机构：

[1] E China Univ Sci & Technol, Sch Pharm, Shanghai 20037, Peoples R China

[2] Myong Ji Univ, Dept Nano Sci & Engn, Dept Chem, Yongin 449728, Kyunggi Do, South Korea

[3] Hanyang Univ, Dept Chem & Appl Chem, Ansan 426791, Kyunggi Do, South Korea

[4] Ulsan Natl Inst Sci & Technol, Interdisciplinary Sch Green Energy, Ulsan 689798, South Korea

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2011年 / 353卷 / 11-12期

关键词：

cyclization; cycloaddition; manganese; oxidation; radical reactions; terpenoids; DIELS-ALDER REACTIONS; STRAIGHTFORWARD SYNTHESIS; RADICAL CYCLIZATIONS; METAL-SALTS; MECHANISMS;

D O I：

10.1002/adsc.201100215

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A new type of terpenoid cyclization directed by a beta-keto ester moiety has been developed, which proceeded by manganese(III)-initiated oxidation of the beta-keto ester, followed by an intramolecular hetero Diels-Alder reaction with the terpenoid chain. This reaction produces polycyclic dihydropyrans in high yields and stereoselectivities under mild conditions.

引用

页码：1913 / 1917

页数：5

共 43 条

[1] LACTONIZATION OF OLEFINS MEDIATED BY MN(OAC)3 - A SONOCHEMICAL APPROACH [J].

ALLEGRETTI, M ;

DANNIBALE, A ;

TROGOLO, C .

TETRAHEDRON, 1993, 49 (46) :10705-10714

[2] Synthesis of five- to seven-membered polyfunctional terpenic carbocycles via Ti(III)-catalyzed radical cyclizations of epoxypolyprenes [J].

Barrero, Alejandro F. ;

del Moral, Jose F. Quilez ;

Herrador, M. Mar ;

Loayza, Ingrid ;

Sanchez, Elena M. ;

Arteaga, Jesus F. .

TETRAHEDRON, 2006, 62 (22) :5215-5222

[3] Biomimetic cyclizations of functionalized isoprenoid polyenes: A cornucopia of synthetic opportunities [J].

Brunoldi, Enrico ;

Luparia, Marco ;

Porta, Alessio ;

Zanoni, Giuseppe ;

Vidari, Giovanni .

CURRENT ORGANIC CHEMISTRY, 2006, 10 (17) :2259-2282

[4]

Cane D.E., 1999, COMPREHENSIVE NATURA, V2

[5]

Demir AS, 2007, CURR ORG SYNTH, V4, P323

[6] ON THE DIRECT FORMATION OF EPISULFONIUM IONS FROM ALKENES - AN APPLICATION TO THE SYNTHESIS OF HIGHER-ORDER CARBOCYCLES VIA EPISULFONIUM ION INITIATED POLYENE CYCLIZATIONS [J].

EDSTROM, ED ;

LIVINGHOUSE, T .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (05) :949-951

[7] Molecular scaffolds for chemical wizardry: Learning nature's rules for terpene cyclases [J].

Greenhagen, B ;

Chappell, J .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2001, 98 (24) :13479-13481

[8]

Handa S, 2000, HELV CHIM ACTA, V83, P2629, DOI 10.1002/1522-2675(20000906)83:9<2629::AID-HLCA2629>3.0.CO

[9]

2-W

[10] TERMINATOR REGULATED MECHANISTIC DIVERGENCE IN BF3MENO2 PROMOTED CASCADE ANNULATIONS OF GEOMETRICALLY DEFINED TRIENOATE DERIVATIVES [J].

HARRING, SR ;

LIVINGHOUSE, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (06) :503-505

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