Stereocontrolled synthesis of all-(E)- and (8Z)-anhydroretinol

被引：24

作者：

Alvarez, R

Iglesias, B

López, S

de Lera, AR ^{[1
]}

机构：

[1] Univ Vigo, Dept Quim Fis & Quim Organ, Vigo 36200, Spain

[2] Univ Santiago Compostela, Dept Quim Organ, E-15706 Santiago, Spain

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(98)01101-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Convergent syntheses of hexaenes anhydroretinol and its (8Z)-isomer are described. Despite the mild reaction conditions for the final step in both cases, a Stille coupling reaction between trienyl triflates and trienyl stannanes, the stereochemical integrity of anhydroretinol is not maintained, due to its intrinsic instability. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：5659 / 5662

页数：4

相关论文

共 32 条

[1]

Alvarez Rosana, 1995, Natural Product Letters, V6, P127, DOI 10.1080/10575639508044100

[2]

[Anonymous], 1982, EUR J BIOCHEM, V129, P1

[3] TOTAL SYNTHESIS OF (+)-MACBECIN-I [J].

BAKER, R ;

CASTRO, JL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (01) :47-65

[4] An efficient method in stannylcupration of a methyl substituted enyne or alkyne by kinetic control using methanol [J].

Betzer, JF ;

Ardisson, J ;

Lallemand, JY ;

Pancrazi, A .

TETRAHEDRON LETTERS, 1997, 38 (13) :2279-2282

[5] INTRACELLULAR SIGNALING BY 14-HYDROXY-4,14-RETRO-RETINOL [J].

BUCK, J ;

DERGUINI, F ;

LEVI, E ;

NAKANISHI, K ;

HAMMERLING, U .

SCIENCE, 1991, 254 (5038) :1654-1656

[6] ANHYDRORETINOL - A NATURALLY-OCCURRING INHIBITOR OF LYMPHOCYTE PHYSIOLOGY [J].

BUCK, J ;

GRUN, F ;

DERGUINI, F ;

CHEN, Y ;

KIMURA, S ;

NOY, N ;

HAMMERLING, U .

JOURNAL OF EXPERIMENTAL MEDICINE, 1993, 178 (02) :675-680

[7] EXPERIMENTAL AND THEORETICAL-ANALYSIS OF THE STERIC TOLERANCE OF THE BINDING-SITE OF BACTERIOOPSIN WITH THE USE OF SIDE-CHAIN METHYL-SHIFTED RETINAL ANALOGS [J].

DELERA, AR ;

IGLESIAS, B ;

RODRIGUEZ, J ;

ALVAREZ, R ;

LOPEZ, S ;

VILLANUEVA, X ;

PADROS, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (31) :8220-8231

[8] INTRACELLULAR SIGNALING ACTIVITY OF SYNTHETIC (14R)-14-HYDROXY-4,14-RETRO-RETINOL, (14S)-14-HYDROXY-4,14-RETRO-RETINOL, AND (14RS)-14-HYDROXY-4,14-RETRO-RETINOL [J].

DERGUINI, F ;

NAKANISHI, K ;

HAMMERLING, U ;

BUCK, J .

BIOCHEMISTRY, 1994, 33 (03) :623-628

[9] SYNTHESIS OF ZYMOSTEROL, FECOSTEROL, AND RELATED BIOSYNTHETIC STEROL INTERMEDIATES [J].

DOLLE, RE ;

SCHMIDT, SJ ;

ERHARD, KF ;

KRUSE, LI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (01) :278-284

[10] Absorption spectra of substances derived from vitamin A. [J].

Edisbury, JR ;

Gillam, AE ;

Heilbron, IM ;

Morton, RA .

BIOCHEMICAL JOURNAL, 1932, 26 :1164-1173

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