A concise total synthesis of (±)-alantrypinone by a novel hetero-Diels-Alder reaction

被引：37

作者：

Kende, AS ^{[1
]}

Fan, JF ^{[1
]}

Chen, ZC ^{[1
]}

机构：

[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 18期

关键词：

D O I：

10.1021/ol030070l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] An efficient total synthesis of (+/-)-alantrypinone (1) and its 17-epi isomer (17) has been accomplished employing a novel aza-Diels-Alder reaction as the key step. The reaction sequence comprises 8 steps starting from anthranilic acid and proceeds in 13.5% overall yield. An interesting anionic equilibration between 1 and its epimer 17 has also been discovered.

引用

收藏

页码：3205 / 3208

页数：4

相关论文

共 18 条

[1] A novel alkaloid serantrypinone and the spiro azaphilone daldinin D from Penicillium thymicola [J].

Ariza, MR ;

Larsen, TO ;

Petersen, BO ;

Duus, JO ;

Christophersen, C ;

Barrero, AF .

JOURNAL OF NATURAL PRODUCTS, 2001, 64 (12) :1590-1592

[2] Free radical cyclizations in alkaloid total synthesis: (+/-)-21-oxogelsemine and (+/-)-gelsemine [J].

Atarashi, S ;

Choi, JK ;

Ha, DC ;

Hart, DJ ;

Kuzmich, D ;

Lee, CS ;

Ramesh, S ;

Wu, SC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (27) :6226-6241

[3] SPIROQUINAZOLINE, A NOVEL SUBSTANCE-P INHIBITOR WITH A NEW CARBON SKELETON, ISOLATED FROM ASPERGILLUS FLAVIPES [J].

BARROW, CJ ;

SUN, HH .

JOURNAL OF NATURAL PRODUCTS, 1994, 57 (04) :471-476

[4] PYRAZINE CHEMISTRY .4. THERMAL [1,4] ELIMINATIONS FROM 3,6-DIHYDROPYRAZINES [J].

BLAKE, KW ;

SAMMES, PG ;

PORTER, AEA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (20) :2494-&

[5]

CASCIERI MA, 1994, J BIOL CHEM, V269, P6587

[6] Synthesis of ent-alantrypinone [J].

Hart, DJ ;

Magomedov, NA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (25) :5892-5899

[7] Synthesis of (-)-alantrypinone [J].

Hart, DJ ;

Magomedov, N .

TETRAHEDRON LETTERS, 1999, 40 (30) :5429-5432

[8] 1-Alkyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones as glycine templates.: Synthesis of Fiscalin B [J].

Hernández, F ;

Buenadicha, FL ;

Avendaño, C ;

Söllhuber, M .

TETRAHEDRON-ASYMMETRY, 2002, 12 (24) :3387-3398

[9] Asymmetric Diels-Alder reactions of 2-azadienes catalyzed by a chiral copper(II) complex. A general route to enantiomerically pure piperidones [J].

Jnoff, E ;

Ghosez, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (11) :2617-2618

[10] UV-guided isolation of alantrypinone, a novel Penicillium alkaloid [J].

Larsen, TO ;

Frydenvang, K ;

Frisvad, JC ;

Christophersen, C .

JOURNAL OF NATURAL PRODUCTS, 1998, 61 (09) :1154-1157