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

[11]

Ichikawa J, 1998, SYNLETT, P927

[12] CARBOHYDRATES AS CHIRAL AUXILIARIES IN STEREOSELECTIVE SYNTHESIS [J].

KUNZ, H ;

RUCK, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (03) :336-358

[13]

Martin R, 1997, SYNLETT, P1414

[14] SUGARS AS CHIRAL AUXILIARIES FOR THE SYNTHESIS OF ENANTIOMERICALLY PURE COMPOUNDS [J].

REISSIG, HU .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (03) :288-290

[15]

ROCHET P, 1993, SYNLETT, P105

[16] [(Z)-GAMMA-[(DIISOPROPYLIDENE-ALPHA-D-MANNOPYRANOSYL)OXY]ALLYL]-TRIBUTYLSTANNANE - A NEW CHIRAL REAGENT FOR THE ASYMMETRIC ALPHA-HYDROXYALLYLATION OF ALDEHYDES [J].

ROUSH, WR ;

VANNIEUWENHZE, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8536-8543

[17] STRUCTURE AND REACTIVITY OF LITHIUM ENOLATES - FROM PINACOLONE TO SELECTIVE C-ALKYLATIONS OF PEPTIDES - DIFFICULTIES AND OPPORTUNITIES AFFORDED BY COMPLEX STRUCTURES [J].

SEEBACH, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (12) :1624-1654

[18] Cross-conjugated cyclopentenone prostaglandins synthesis of Δ7-10-chloro-15-deoxy PGA1 ethyl ester [J].

Tius, MA ;

Busch-Petersen, J ;

Yamashita, M .

TETRAHEDRON LETTERS, 1998, 39 (24) :4219-4222

[19] Asymmetric nucleophilic addition to β- and γ-alkoxy aldehydes using carbohydrate as a chiral auxiliary [J].

Yoshida, T ;

Chika, J ;

Takei, H .

TETRAHEDRON LETTERS, 1998, 39 (24) :4305-4308

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