Progress toward the total synthesis of bacchopetiolone:: Application of a tandem aromatic oxidation/Diels-Alder reaction

被引：45

作者：

Berube, Amelie ^{[1
]}

Drutu, Ioana ^{[1
]}

Wood, John L. ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 24期

关键词：

D O I：

10.1021/ol061737h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective synthesis of the bacchopetiolone (1) carbocyclic core using a tandem phenolic oxidation/Diels-Alder reaction is described.

引用

页码：5421 / 5424

页数：4

共 9 条

[1]

BARTON DHR, 1979, TETRAHEDRON LETT, P2291

[2]

BIERNACKI W, 1979, SYNTHESIS-STUTTGART, P37

[3] Reactive dienes: Intramolecular aromatic oxidation of 3-(2-hydroxyphenyl)-propionic acids [J].

Drutu, I ;

Njardarson, JT ;

Wood, JL .

ORGANIC LETTERS, 2002, 4 (04) :493-496

[4] Inverse-electron-demand Diels-Alder reactions of masked o-benzoquinones with enol ethers and styrene [J].

Gao, SY ;

Ko, S ;

Lin, YL ;

Peddinti, RK ;

Liao, CC .

TETRAHEDRON, 2001, 57 (02) :297-308

[5] SYNTHESES OF SUBSTITUTED SUCCINIMIDES BY RADICAL BETA-FRAGMENTATION OF BICYCLIC CARBINOL AMIDES - A NEW EXPEDITIOUS SYNTHESIS OF 2-[2-(METHOXYCARBONYL)ETHYL]-3-[(METHOXYCARBONYL)METHYL]3-METHYLSUCCINIMIDE, THE RING-B IMIDE OF VITAMIN-B-12 [J].

HERNANDEZ, R ;

SUAREZ, E ;

MELIAN, D .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (10) :2766-2772

[6]

HERNANDEZ R, 1995, HETEROCYCLES, V41, P439

[7] Complete π-facial diastereoselectivity in Diels-Alder reactions of dissymmetric 2,4-cyclohexadienones [J].

Hou, HF ;

Peddinti, RK ;

Liao, CC .

ORGANIC LETTERS, 2002, 4 (15) :2477-2480

[8] CONVERSION OF ALIPHATIC AMIDES INTO AMINES WITH [I,I-BIS(TRIFLUOROACETOXY)IODO]BENZENE .1. SCOPE OF THE REACTION [J].

LOUDON, GM ;

RADHAKRISHNA, AS ;

ALMOND, MR ;

BLODGETT, JK ;

BOUTIN, RH .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (22) :4272-4276

[9] AN UNUSUAL DIMERIC SESQUITERPENE AND OTHER CONSTITUENTS FROM CHILEAN BACCHARIS SPECIES [J].

ZDERO, C ;

BOHLMANN, F ;

NIEMEYER, HM .

PHYTOCHEMISTRY, 1991, 30 (05) :1597-1601

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