Synthesis of (-)-alantrypinone

被引：39

作者：

Hart, DJ ^{[1
]}

Magomedov, N ^{[1
]}

机构：

[1] Ohio State Univ, Dept Chem, Columbus, OH 43210 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 30期

关键词：

D O I：

10.1016/S0040-4039(99)01005-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of (-)-alantrypinone is described. The synthesis features the use of [Me3AlSPh]Li as a promoter of a 4-iminobenzoxazine to 4-quinazolinone rearrangement and as a reagent for the deprotection of an Fmoc-protected amino acid derivative. (C) 1999 Elsevier Science Ltd, All rights reserved.

引用

收藏

页码：5429 / 5432

页数：4

相关论文

共 12 条

[1] 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

[2] ((9-FLUORENYLMETHYL)OXY)CARBONYL (FMOC) AMINO-ACID CHLORIDES - SYNTHESIS, CHARACTERIZATION, AND APPLICATION TO THE RAPID SYNTHESIS OF SHORT PEPTIDE SEGMENTS [J].

CARPINO, LA ;

COHEN, BJ ;

STEPHENS, KE ;

SADATAALAEE, SY ;

TIEN, JH ;

LANGRIDGE, DC .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) :3732-3734

[3] Spiroquinazoline support studies: New cascade reactions based on the Morin rearrangement [J].

Hart, DJ ;

Magomedov, N .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :2990-2991

[4]

He F, 1997, SYNLETT, P483

[5] Rearrangement of 4-imino-4H-3,1-benzoxazines to 4-quinazolinones via amidine carboxamides [J].

He, F ;

Snider, BB .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1397-1399

[6] ALDOL REACTION OF ALUMINUM ENOLATE RESULTING FROM 1,4-ADDITION OF ME2ALSPH TO ALPHA,BETA-UNSATURATED CARBONYL COMPOUND - ALPHA 1-ACYLETHENYL ANION EQUIVALENT [J].

ITOH, A ;

OZAWA, S ;

OSHIMA, K ;

NOZAKI, H .

TETRAHEDRON LETTERS, 1980, 21 (04) :361-364

[7] 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

[8] SYNTHESIS AND REARRANGEMENT OF 4-IMINO-4 H-3,1-BENZOXAZINES [J].

MAZURKIEWICZ, R .

MONATSHEFTE FUR CHEMIE, 1989, 120 (11) :973-980

[9] TOTAL SYNTHESIS OF (+)-TRYPTOQUIVALINE-G AND (-)-TRYPTOQUIVALINE-G BY BIOMIMETIC DOUBLE CYCLIZATION [J].

NAKAGAWA, M ;

TANIGUCHI, M ;

SODEOKA, M ;

ITO, M ;

YAMAGUCHI, K ;

HINO, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (11) :3709-3710

[10] SYNTHESIS OF THE OXINDOLE ALKALOID (-)-HORSFILINE [J].

PELLEGRINI, C ;

STRASSLER, C ;

WEBER, M ;

BORSCHBERG, HJ .

TETRAHEDRON-ASYMMETRY, 1994, 5 (10) :1979-1992