Isomerization-cyclization approach to the synthesis of 2-hydroxy-5-alkylidene-cyclopent-2-enones

被引：17

作者：

Forest, J

Bee, C

Cordaro, F

Tius, MA

机构：

[1] Univ Hawaii, Dept Chem, Honolulu, HI 96822 USA

[2] Canc Res Ctr Hawaii, Honolulu, HI 96813 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 22期

关键词：

D O I：

10.1021/ol035498z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] Propargyl vinyl ketones that are derived from the addition of 1-lithio-1-methoxymethoxy-2-ynes to morpholino enamides undergo isomerization followed by cyclization to alpha-methylene cyclopentenones upon exposure to silica gel.

引用

页码：4069 / 4072

页数：4

共 13 条

[1] Convergent cyclopentannelation process [J].

Bee, C ;

Tius, MA .

ORGANIC LETTERS, 2003, 5 (10) :1681-1684

[2]

Habermas K.L., 1994, ORG REACTIONS, V45, P1

[3]

Hashmi ASK, 1998, TETRAHEDRON LETT, V39, P7491

[4]

HOFF S, 1968, RECL TRAV CHIM PAY-B, V87, P916

[5] Asymmetric cyclopentannelation. Axial to tetrahedral chirality transfer [J].

Hu, HP ;

Smith, D ;

Cramer, RE ;

Tius, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (42) :9895-9896

[6] ENYNONES IN ORGANIC-SYNTHESIS .1. SPIROANNULATION BY TANDEM OXY-COPE REARRANGEMENT-ELECTROCYCLIC RING-CLOSURE [J].

JACOBI, PA ;

ARMACOST, LM ;

KRAVITZ, JI ;

MARTINELLI, MJ ;

SELNICK, HG .

TETRAHEDRON LETTERS, 1988, 29 (52) :6865-6868

[7] Parallel synthesis and biocatalytic amplification of a cross-conjugated cyclopentenone library [J].

Jang, WB ;

Hu, HP ;

Lieberman, MM ;

Morgan, JA ;

Stergiades, IA ;

Clark, DS ;

Tius, MA .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2001, 3 (04) :346-353

[8] CRYSTAL AND MOLECULAR-STRUCTURE OF 1-(IODODIMETHYLSILYLMETHYL)PIPERIDONE-2 [J].

MACHARASHVILI, AA ;

SHKLOVER, VE ;

STRUCHKOV, YT ;

BAUKOV, YI ;

KRAMAROVA, EP ;

OLENEVA, GI .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 327 (02) :167-172

[9]

Schultz-Fademrecht C, 2002, ANGEW CHEM INT EDIT, V41, P1532, DOI 10.1002/1521-3773(20020503)41:9<1532::AID-ANIE1532>3.0.CO

[10]

2-J

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