Asymmetric cyclopentannelation. Chiral auxiliary on the allene

被引：54

作者：

Harrington, PE ^{[1
]}

Tius, MA ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 16期

关键词：

D O I：

10.1021/ol0001362

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] An enantioselective variant of the synthesis of cross-conjugated cyclopentenones, based on D-glucose-derived chiral auxiliaries, is described. Minor modification of the method makes it applicable to the preparation of both enantiomeric series of products. Both enantiomers of the key intermediate in our roseophilin synthesis have been prepared.

引用

页码：2447 / 2450

页数：4

共 19 条

[1]

BASHA A, 1977, TETRAHEDRON LETT, V18, P4171, DOI DOI 10.1016/S0040-4039(01)83457-2

[2]

BESSODES M, 1988, SYNTHESIS-STUTTGART, P560

[3]

Bollenback G. N., 1963, METHODS CARBOHYDRATE, V2, P326

[4]

CHARETTE AB, 1995, SYNLETT, P1197

[5] Naphthyl 3,4,6-tri-O-methyl-beta-D-glucopyranoside as a chiral auxiliary in an asymmetric 1,4-addition reaction [J].

Chiappe, C ;

LoMoro, G ;

Munforte, P .

TETRAHEDRON-ASYMMETRY, 1997, 8 (14) :2311-2317

[6] Arabinose as a chiral auxiliary for the asymmetric α-hydroxyallylation of aldehydes to syn-1,2-diols [J].

Chika, J ;

Takei, H .

TETRAHEDRON LETTERS, 1998, 39 (07) :605-608

[7] AUXILIARY INDUCED RHO-STEREOCONTROL IN ACETALOXYALKYL RADICAL-ADDITION REACTIONS [J].

GARNER, PP ;

COX, PB ;

KLIPPENSTEIN, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (14) :4183-4184

[8] A formal total synthesis of roseophilin: Cyclopentannelation approach to the macrocyclic core [J].

Harrington, PE ;

Tius, MA .

ORGANIC LETTERS, 1999, 1 (04) :649-651

[9]

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

[10] 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

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