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)-γ-alkylidenebutenolides

An antibiotic lissoclinolide has been synthesized from propargyl alcohol in 9 steps and in 32% overall yield via (i) hydrogen transfer hydrozirconation of TBS-protected propargyl alcohol with i-BuZrCp 2Cl, (ii) Pd-catalyzed trans-selective cross coupling of the hydrozirconation product with a key 1,...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 40; no. 3; pp. 431 - 434
Main Authors Xu, Caiding, Negishi, Ei-ichi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.01.1999
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
GAMMA-ALKYLIDENEBUTENOLIDES
ALKYNOIC ACIDS
DIENES
CONVENIENT PROCEDURE
STEREOSELECTIVE SYNTHESIS
CYCLIZATION
Online AccessGet full text

Cover

More Information
Summary:An antibiotic lissoclinolide has been synthesized from propargyl alcohol in 9 steps and in 32% overall yield via (i) hydrogen transfer hydrozirconation of TBS-protected propargyl alcohol with i-BuZrCp 2Cl, (ii) Pd-catalyzed trans-selective cross coupling of the hydrozirconation product with a key 1,1-dibromoalkene intermediate 5 and (iii) Ag-catalyzed lactonization of a trienynoic acid precursor 2. [Display omitted]
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)02394-6