Synthetic applications of asymmetric Horner-Wadsworth-Emmons condensations: Approaches to marine natural products

被引：0

作者：

Tullis, JS ^{[1
]}

Helquist, P

Rein, T

机构：

[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA

[2] Tech Univ Denmark, Dept Organ Chem, DK-2800 Lyngby, Denmark

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 1999年 / 144卷

关键词：

asymmetric Horner-Wadsworth-Emmons condensation; chiral phosphonate; desymmetrization; doliculide; meso-dialdehyde;

D O I：

10.1080/10426509908039523

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Asymmetric HWE condensations of meso-dialdehyde 1 with chiral phosphonates containing 8-phenylmenthol very directly generate chiral moieties that are seen in a number of cytotoxic natural products. The HWE reactions proceed in good yields with synthetically useful geometric and diastereoselectivities. Also, we demonstrate the applicability of the HWE products to the synthesis of biologically active marine natural products.

引用

页码：165 / 168

页数：4

共 12 条

[1]

ISHIWATA H, 1994, TETRAHEDRON, V50, P12853

[2] TOTAL SYNTHESIS OF DOLICULIDE, A POTENT CYTOTOXIC CYCLODEPSIPEPTIDE FROM THE JAPANESE SEA HARE DOLABELLA-AURICULARIA [J].

ISHIWATA, H ;

SONE, H ;

KIGOSHI, H ;

YAMADA, K .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) :4712-4713

[3] ISOLATION AND STEREOSTRUCTURE OF DOLICULIDE, A CYTOTOXIC CYCLODEPSIPEPTIDE FROM THE JAPANESE SEA HARE DOLABELLA-AURICULARIA [J].

ISHIWATA, H ;

NEMOTO, T ;

OJIKA, M ;

YAMADA, K .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) :4710-4711

[4] ASYMMETRIC HORNER-WADSWORTH-EMMONS REACTIONS USING MESO DIALDEHYDES AS SUBSTRATES [J].

KANN, N ;

REIN, T .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3802-3804

[5] A NEW CANDIDATE FOR A PROPERLY SUBSTITUTED CD RING COMPONENT OF VITAMIN-D-3 VIA INTRAMOLECULAR ASYMMETRIC OLEFINATION OF A 1,3-CYCLOPENTANEDIONE DERIVATIVE [J].

MANDAI, T ;

KAIHARA, Y ;

TSUJI, J .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) :5847-5849

[6]

Pettit G. R., 1995, U.S. Patent, Patent No. [5430053, 5,430,053]

[7] ISOLATION AND STRUCTURE OF THE CANCER CELL-GROWTH INHIBITOR DICTYOSTATIN-1 [J].

PETTIT, GR ;

CICHACZ, ZA ;

GAO, F ;

BOYD, MR ;

SCHMIDT, JM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (09) :1111-1112

[8] Recent advances in asymmetric Wittig-type reactions [J].

Rein, T ;

Reiser, O .

ACTA CHEMICA SCANDINAVICA, 1996, 50 (04) :369-379

[9] Formation of non-racemic E- and Z-olefins based on discrimination of enantiotopic carbonyl groups in α-diketones by a chiral phosphonate reagent [J].

Tanaka, K ;

Watanabe, T ;

Ohta, Y ;

Fuji, K .

TETRAHEDRON LETTERS, 1997, 38 (52) :8943-8946

[10] DIFFERENTIATION OF ENANTIOTOPIC CARBONYL GROUPS BY THE HORNER-WADSWORTH-EMMONS REACTION [J].

TANAKA, K ;

OHTA, Y ;

FUJI, K ;

TAGA, T .

TETRAHEDRON LETTERS, 1993, 34 (25) :4071-4074

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