First enantioselective synthesis of manoalide: application of aldehyde-dioxinone enantioselective condensation

被引：31

作者：

Soriente, A ^{[1
]}

De Rosa, M ^{[1
]}

Apicella, A ^{[1
]}

Scettri, A ^{[1
]}

Sodano, G ^{[1
]}

机构：

[1] Univ Salerno, Dipartimento Chim, I-84081 Baronissi, SA, Italy

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 23期

关键词：

D O I：

10.1016/S0957-4166(99)00529-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Manoalide, an analgesic and anti-inflammatory sesterterpene, has been stereoselectively synthesized for the first time. The C-4 stereogenic centre has been introduced in an early step by enantioselective aldol condensation using a Ti(OiPr)(4)/(R)-(+)-binol complex. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4481 / 4484

页数：4

共 21 条

[1] 2 SYNTHESES OF MANOALIDE VIA HETEROATOM-ASSISTED ALKYNE CARBOMETALLATION [J].

BURY, P ;

HAREAU, G ;

KOCIENSKI, P ;

DHANAK, D .

TETRAHEDRON, 1994, 50 (29) :8793-8808

[2] 1,3-SYN DIASTEREOSELECTIVE REDUCTION OF BETA-HYDROXYKETONES UTILIZING ALKOXYDIALKYLBORANES [J].

CHEN, KM ;

HARDTMANN, GE ;

PRASAD, K ;

REPIC, O ;

SHAPIRO, MJ .

TETRAHEDRON LETTERS, 1987, 28 (02) :155-158

[3]

Coombs J, 1998, SYNTHESIS-STUTTGART, P1367

[4] Synthesis and comparison of the antiinflammatory activity of manoalide and cacospongionolide B analogues [J].

De Rosa, M ;

Giordano, S ;

Scettri, A ;

Sodano, G ;

Soriente, A ;

Pastor, PG ;

Alcaraz, MJ ;

Payá, M .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (17) :3232-3238

[5]

de Silva E.D., 1980, TETRAHEDRON LETT, V21, P1611, DOI [10.1016/S0040-4039(00)77766-5, DOI 10.1016/S0040-4039(00)77766-5]

[6] TOTAL SYNTHESIS OF MANOALIDE [J].

GARST, ME ;

TALLMAN, EA ;

BONFIGLIO, JN ;

HARCOURT, D ;

LJUNGWE, EB ;

TRAN, A .

TETRAHEDRON LETTERS, 1986, 27 (38) :4533-4536

[7] HIGHLY EFFICIENT TOTAL SYNTHESIS OF MANOALIDE AND SECO-MANOALIDE VIA PD(0) CATALYZED COUPLING OF ALLYLHALIDE WITH CO AND 2-SILYL-4-STANNYLFURAN [J].

KATSUMURA, S ;

FUJIWARA, S ;

ISOE, S .

TETRAHEDRON LETTERS, 1988, 29 (10) :1173-1176

[8] TOTAL SYNTHESIS OF MANOALIDE AND SECO-MANOALIDE [J].

KATSUMURA, S ;

FUJIWARA, S ;

ISOE, S .

TETRAHEDRON LETTERS, 1985, 26 (47) :5827-5830

[9]

KOBAYASHI M, 1994, CHEM PHARM BULL, V42, P265

[10] Apparent catalytic generation of chiral metal enolates:: Enantioselective dienolate additions to aldehydes mediated by Tol-BINAP•Cu(II) fluoride complexes [J].

Krüger, J ;

Carreira, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (04) :837-838

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