Microwave-assisted rearrangement of vinylaziridines to 3-pyrrolines: Formal synthesis of (-)-anisomycin

被引：21

作者：

Hirner, S ^{[1
]}

Somfai, P ^{[1
]}

机构：

[1] KTH Chem Sci & Engn, S-10044 Stockholm, Sweden

来源：

SYNLETT | 2005年 / 20期

关键词：

vinylaziridines; pyrrolines; rearrangement; ring expansion; total synthesis;

D O I：

10.1055/s-2005-921934

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient microwave-assisted rearrangement of activated vinylaziridines to 3-pyrrolines is described. The rearrangement proceeds in good to excellent yields and is mediated by NaI or LiI in MeCN at elevated temperatures. The synthetic utility of this reaction is shown in an efficient formal total synthesis of the antibiotic (-)-anisomycin.

引用

收藏

页码：3099 / 3102

页数：4

相关论文

共 40 条

[1] 3-PYRROLINE N-OXIDE BIS(CARBAMATE) TUMOR INHIBITORS AS ANALOGS OF INDICINE N-OXIDE [J].

ANDERSON, WK ;

MILOWSKY, AS .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (11) :2144-2147

[2] Direct synthesis of aliphatic vinyl aziridines [J].

Arini, LG ;

Sinclair, A ;

Szeto, P ;

Stockman, RA .

TETRAHEDRON LETTERS, 2004, 45 (08) :1589-1591

[3] REACTIVE INTERMEDIATES .8. THERMOLYSIS OF N-(VINYLAZIRIDINYL)-BENZOAXAZOLINONES . SOME NEW HETEROCYCLIC REARRANGEMENTS [J].

ATKINSON, RS ;

REES, CW .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (05) :778-&

[4] Recent advances in the Baylis-Hillman reaction and applications [J].

Basavaiah, D ;

Rao, AJ ;

Satyanarayana, T .

CHEMICAL REVIEWS, 2003, 103 (03) :811-891

[5] A NEW SYNTHESIS OF (-)-ANISOMYCIN AND ITS DEMETHOXY ANALOG FROM D-RIBOSE [J].

BUCHANAN, JG ;

MACLEAN, KA ;

WIGHTMAN, RH ;

PAULSEN, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (07) :1463-1470

[6] ENANTIOSPECIFIC SYNTHESIS OF 3-PYRROLINES - A ROUTE TO NOVEL POLYHYDROXYLATED PYRROLIDINES [J].

BURLEY, I ;

HEWSON, AT .

TETRAHEDRON LETTERS, 1994, 35 (38) :7099-7102

[7] Reaction of α-(N-carbamoyl)alkylcuprates with propargyl substrates:: Synthetic route to a-amino allenes and Δ3-pyrrolines [J].

Dieter, RK ;

Chen, NY ;

Yu, HY ;

Nice, LE ;

Gore, VK .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06) :2109-2119

[8] Synthesis of 3-pyrrolines, annulated 3-pyrrolines, and pyrroles from α-Amino allenes [J].

Dieter, RK ;

Yu, H .

ORGANIC LETTERS, 2001, 3 (24) :3855-3858

[9] Regioselective Rh-catalyzed allylic amination/ring-closing metathesis approach to monocyclic azacycles: Diastereospecific construction of 2,5-disubstituted pyrrolines [J].

Evans, PA ;

Robinson, JE .

ORGANIC LETTERS, 1999, 1 (12) :1929-1931

[10] TRANSFORMATION OF N-TOSYL-2-(1,3-BUTADIENYL)AZIRIDINE INTO N-TOSYL-2-ETHENYL-3-PYRROLINE [J].

FUGAMI, K ;

MIURA, K ;

MORIZAWA, Y ;

OSHIMA, K ;

UTIMOTO, K ;

NOZAKI, H .

TETRAHEDRON, 1989, 45 (10) :3089-3098

← 1 2 3 4 →