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
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
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.