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,...
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Published in | Tetrahedron letters Vol. 40; no. 3; pp. 431 - 434 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
15.01.1999
Elsevier |
Subjects | |
Online Access | Get full text |
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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.
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ISSN: | 0040-4039 1873-3581 |
DOI: | 10.1016/S0040-4039(98)02394-6 |