Novel tandem "Ene-ISMS" methodology.: Efficient and versatile assembly of a pseudomonic acid C analogue.

被引：24

作者：

Markó, IE ^{[1
]}

Plancher, JM ^{[1
]}

机构：

[1] Univ Catholique Louvain, Dept Chim, Chim Organ Lab, B-1348 Louvain, Belgium

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 28期

关键词：

D O I：

10.1016/S0040-4039(99)00996-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The pseudomonic acid C analogue 19 can be readily constructed using a novel tandem methodology involving, as a key-step, an ene-reaction followed by a concomitant Intramolecular Silyl-Mediated Sakurai (ISMS) cyclisation. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：5259 / 5262

页数：4

共 33 条

[1] CHEMISTRY OF PSEUDOMONIC ACID .1. ABSOLUTE-CONFIGURATION OF PSEUDOMONIC ACID-A [J].

ALEXANDER, RG ;

CLAYTON, JP ;

LUK, K ;

ROGERS, NH ;

KING, TJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (06) :561-565

[2]

BADDER A, 1887, CORRES BL SCHWEIZ AE, V17, P385

[3] TOTAL SYNTHESIS OF PSEUDOMONIC ACID-C [J].

BARRISH, JC ;

LEE, HL ;

MITT, T ;

PIZZOLATO, G ;

BAGGIOLINI, EG ;

USKOKOVIC, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) :4282-4295

[4] AN APPROACH TO PSEUDOMONIC ACIDS FROM ACETYLENIC PRECURSORS - SYNTHESIS OF 2-(HYDROXYMETHYL)-3-BUTYN-1-OL [J].

BATES, HA ;

FARINA, J ;

TONG, M .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14) :2637-2641

[5] TOTAL SYNTHESIS OF (+)-METHYL PSEUDOMONATE-C FROM CARBOHYDRATES [J].

BEAU, JM ;

ABURAKI, S ;

POUGNY, JR ;

SINAY, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (03) :621-622

[6] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938

[7] CHEMISTRY OF PSEUDOMONIC ACID .3. REARRANGEMENT OF PSEUDOMONIC ACID A IN ACID AND BASIC SOLUTION [J].

CLAYTON, JP ;

OLIVER, RS ;

ROGERS, NH ;

KING, TJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (03) :838-846

[8] THE CHEMISTRY OF PSEUDOMONIC ACID .2. DEHYDRATIVE CYCLIZATION OF ALPHA-ACYLAMINO KETONES TO OXAZOLES [J].

CRIMMIN, MJ ;

OHANLON, PJ ;

ROGERS, NH ;

SIME, FM ;

WALKER, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (11) :2059-2063

[9] THE CHEMISTRY OF PSEUDOMONIC ACID .10. PREPARATION OF HETEROCYCLIC-DERIVATIVES [J].

CRIMMIN, MJ ;

OHANLON, PJ ;

ROGERS, NH ;

WALKER, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (11) :2047-2057

[10] SYNTHETIC APPLICATION OF A SUBSTITUENT CONTROLLED CLAISEN REARRANGEMENT - PREPARATION OF ADVANCED CHIRAL INTERMEDIATES FOR THE SYNTHESIS OF PSEUDOMONIC ACIDS [J].

CURRAN, DP ;

SUH, YG .

TETRAHEDRON LETTERS, 1984, 25 (38) :4179-4182

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