Stereocontrolled synthesis of lissoclinolide by sequential transition metal-catalyzed lactonization/cross-coupling reactions

被引：81

作者：

Rossi, R

Bellina, F

Biagetti, M

Mannina, L

机构：

[1] Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy

[2] Univ Molise, Corso Laurea Sci Ambientali, I-86170 Isernia, Italy

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 42期

关键词：

D O I：

10.1016/S0040-4039(98)01705-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lissoclinolide, 1, which is an antibiotic butenolide isolated front a Tunicate, has been synthesized stereoselectively by a reaction sequence in which the Ag(I)-catalyzed lactonization of (2E,6E)-2-bromo-8-hydroxy-2,6-octadien-4-ynoic acid, (E,E)-13, and the Pd/Cu-catalyzed cross-coupling reaction of so obtained (Z)-2-bromo-5-[(E)-4-hydroxy-2-butenylidene]-5H-furan-2-one, (Z,E)-14, with (E)-3-hydroxyl-1-propenyltributylstannane, 15, have been used as the key steps. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：7799 / 7802

页数：4

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