A highly efficient and selective synthesis of lissoclinolide featuring hydrogen transfer hydrozirconation, trans-selective Pd-catalyzed cross coupling of alkenylzirconiums with 1,1-dibromoalkenes and Ag-catalyzed lactonization providing (Z)-gamma-alkylidenebutenolides

Authors
Xu, CD Negishi, E
Citation
Cd. Xu et E. Negishi, A highly efficient and selective synthesis of lissoclinolide featuring hydrogen transfer hydrozirconation, trans-selective Pd-catalyzed cross coupling of alkenylzirconiums with 1,1-dibromoalkenes and Ag-catalyzed lactonization providing (Z)-gamma-alkylidenebutenolides, TETRAHEDR L, 40(3), 1999, pp. 431-434
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
3
Year of publication
1999
Pages
431 - 434
Database
ISI
SICI code
0040-4039(19990115)40:3<431:AHEASS>2.0.ZU;2-Z
Abstract
An antibiotic lissoclinolide has been synthesized from propargyl alcohol in 9 steps and in 32% overall yield via (i) hydrogen transfer hydrozirconatio n of TBS-protected propargyl alcohol with i-BuZrCp2Cl, (ii) Pd-catalyzed tr ans-selective cross coupling of the hydrozirconation product with a key 1,1 -dibromoalkene intermediate 5 and (iii) Ag-catalyzed lactonization of a tri enynoic acid precursor 2. (C) 1998 Elsevier Science Ltd. All rights reserve d.