A novel route to preussomerins via 2-arylacetal anions

被引：29

作者：

Ragot, JP ^{[1
]}

Prime, ME ^{[1
]}

Archibald, SJ ^{[1
]}

Taylor, RJK ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 11期

关键词：

D O I：

10.1021/ol005881t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Dimerization of salicyladehydes provided 6H,12H-6,12-epoxydibenzo[b,f][1,5]dioxocins in multigram quantities. Deprotonation-allylation of the benzylic acetals followed by further functionalization of the diallyl derivative and double Friedel-Crafts cyclization gave a novel preussomerin analogue which possessed the full carbon skeleton of the natural products.

引用

页码：1613 / 1616

页数：4

共 20 条

[1] THE SYNTHESIS OF SPIRO[ADAMANTANE-[1,2]DIOXETANES] [J].

ADAM, W ;

ENCARNACION, LAA .

CHEMISCHE BERICHTE-RECUEIL, 1982, 115 (07) :2592-2605

[2] Manumycin A: Synthesis of the (+)-enantiomer and revision of stereochemical assignment [J].

Alcaraz, L ;

Macdonald, G ;

Ragot, JP ;

Lewis, N ;

Taylor, RJK .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (11) :3526-3527

[3] Total syntheses of (±)-preussomerins G and I [J].

Chi, S ;

Heathcock, CH .

ORGANIC LETTERS, 1999, 1 (01) :3-5

[4]

DAMON RE, 1975, TETRAHEDRON LETT, P4551

[5] REACTIONS OF BENZALDEHYDE ACETALS WITH BUTYL-LITHIUM - A STEREOSPECIFIC OLEFIN SYNTHESIS [J].

HINES, JN ;

PEAGRAM, MJ ;

WHITHAM, GH ;

WRIGHT, M .

CHEMICAL COMMUNICATIONS, 1968, (24) :1593-&

[6]

HUET F, 1979, SYNTHESIS-STUTTGART, P33

[7]

Johnson C. K., 1976, ORNL5138

[8] A FACILE SYNTHESIS OF ANHYDRO-DIMERS OF ORTHO-HYDROXYBENZALDEHYDES [J].

KULKARNI, VS ;

HOSANGADI, BD .

SYNTHETIC COMMUNICATIONS, 1986, 16 (02) :191-193

[9] STEREOELECTRONIC EFFECTS .5. STEREOELECTRONIC PROPERTIES, STEREOSPECIFICITY, AND STABILIZATION OF ALPHA-OXA AND ALPHA-THIA CARBANIONS [J].

LEHN, JM ;

WIPFF, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (24) :7498-7505

[10] Ras farnesyltransferase: A new therapeutic target [J].

Leonard, DM .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (19) :2971-2990

← 1 2 →