A synthetic approach to palmerolides via Negishi cross coupling. The challenge of the C15-C16 bond formation

被引：10

作者：

Carrillo, Jokin ^{[1
]}

Gomez, Alex ^{[1
]}

Costa, Anna M. ^{[1
]}

Fernandez, Patricia ^{[1
]}

Isart, Caries ^{[1
]}

Sidera, Mireia ^{[1
]}

Vilarrasa, Jaume ^{[1
]}

机构：

[1] Univ Barcelona, Fac Quim, Dept Quim Organ, E-08028 Barcelona, Catalonia, Spain

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 33期

关键词：

Negishi cross-coupling reactions; Screening of phosphine ligands; Palmerolides; Melanoma-inhibiting macrolides; ENANTIOSELECTIVE TOTAL-SYNTHESIS; ACETATE ALDOL REACTIONS; MARINE NATURAL-PRODUCT; ORGANOTIN COMPOUNDS; STILLE REACTION; CHIRAL AUXILIARIES; REVISED STRUCTURES; FORMING PROCESSES; A SYNTHESIS; IN-SITU;

D O I：

10.1016/j.tetlet.2014.06.066

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The esterification of fragment C1-C8 (2) with fragment C16-C23 (3) to give iodo derivative 4, followed by a Pd-catalysed coupling with a C9-C15 fragment (7 or 8), may provide a common precursor of most palmerolides. Ligands and reaction conditions were exhaustively examined to perform the C15-C16 bond formation via Negishi reaction. With simple models, pre-activated Pd-Xantphos and Pd-DPEphos complexes were the most efficient catalysts at RT. Zincation of the C9-C15 fragment (8) and cross coupling with 4 required 3 equiv of t-BuLi, 10 mol % of Pd-Xantphos and 60 degrees C. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：4623 / 4627

页数：5

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