Modular synthesis of tetrahydrofluorenones from 5-alkylidene Meldrum's acids

被引：33

作者：

Fillion, Eric ^{[1
]}

Dumas, Aaron M. ^{[1
]}

Hogg, Sylvia A. ^{[1
]}

机构：

[1] Univ Waterloo, Dept Chem, Waterloo, ON N2L 3G1, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 26期

关键词：

DIELS-ALDER REACTIONS; TAIWANIA-CRYPTOMERIOIDES; THUJA-STANDISHII; PYROLYTIC GENERATION; DITERPENES; BARK; DERIVATIVES; ROUTE; (+/-)-DICHROANAL-B; PRECURSOR;

D O I：

10.1021/jo0618876

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The one-pot synthesis of tetrahydrofluorenones, the core 6-5-6 tricyclic structural motif found in norditerpenoid natural products, from alkylidene Meldrum's acids via thermal Diels-Alder/BF3 center dot OEt2-catalyzed Friedel-Crafts acylation reactions is described. A series of tetrahydrofluorenones was assembled in good yields, and the Diels-Alder/Friedel-Crafts acylation protocol allowed modification of the substitution within the rings.

引用

页码：9899 / 9902

页数：4

共 41 条

[1] Diels-Alder reactions with cyclic sulfones: VII. Synthesis of 1-benzothiophene 1,1-dioxide derivatives [J].

Andreev, GN ;

Shul'ts, EE ;

Volkov, AA ;

Shakirov, MM ;

Bagryanskaya, IY ;

Gatilov, YV ;

Tolstikov, GA .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 40 (06) :854-865

[2]

[Anonymous], RUSS J ORG CHEM

[3] General route to 4a-methylhydrofluorene diterpenoids:: Total syntheses of (±)-taiwaniaquinones D and H, (±)-taiwaniaquinol B, (±)-dichroanal B, and (±)-dichroanone [J].

Banerjee, M ;

Mukhopadhyay, R ;

Achari, B ;

Banerjee, AK .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (07) :2787-2796

[4] First total synthesis of the 4a-methyltetrahydrofluorene diterpenoids (±)-dichroanal B and (±)-dichroanone [J].

Banerjee, M ;

Mukhopadhyay, R ;

Achari, B ;

Banerjee, AK .

ORGANIC LETTERS, 2003, 5 (21) :3931-3933

[5] STUDIES ON THE SYNTHESIS OF APHIDICOLIN - THE DIELS-ALDER ROUTE TO SPIROCYCLIC INTERMEDIATES [J].

BELL, VL ;

HOLMES, AB ;

HSU, SY ;

MOCK, GA ;

RAPHAEL, RA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (08) :1507-1514

[6] AN IMPROVED SYNTHESIS OF 1,4-DITHIASPIRO[4.5] DECAN-8-ONE (CYCLOHEXANE-1,4-DIONE MONOTHIOACETAL) [J].

BELL, VL ;

HOLMES, AB .

SYNTHETIC COMMUNICATIONS, 1982, 12 (04) :323-326

[7] DIELS-ALDER REACTIONS ON LINEAR POLYENES, SELECTIVELY PROTECTED AS THEIR TRICARBONYL-IRON COMPLEXES [J].

BENVEGNU, T ;

MARTELLI, J ;

GREE, R ;

TOUPET, L .

TETRAHEDRON LETTERS, 1990, 31 (22) :3145-3148

[8] DIELS-ALDER REACTIONS WITH DIACCEPTOR-SUBSTITUTED METHYLENE-CYCLOPROPANES - A NEW ASPECT FOR THE TWOFOLD NUCLEOPHILIC-SUBSTITUTION AT CYCLOPROPANE [J].

BENZING, M ;

VILSMAIER, E ;

MARTINI, H ;

MICHELS, G ;

ANDERS, E .

CHEMISCHE BERICHTE, 1989, 122 (07) :1277-1284

[9] EVIDENCE FOR PYROLYTIC GENERATION OF METHYLENE KETENE (PROPADIENONE) [J].

BROWN, RFC ;

EASTWOOD, FW ;

MCMULLEN, GL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (23) :7421-7422

[10] METHYLENE-KETENES AND METHYLENE-CARBENES .7. EVIDENCE FOR PYROLYTIC GENERATION OF METHYLENEKETENE (PROPADIENONE) [J].

BROWN, RFC ;

EASTWOOD, FW ;

MCMULLEN, GL .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1977, 30 (01) :179-193

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