Synthesis of vinylcyclopropanes via palladium-catalyzed coupling of cyclopropylzinc halides with vinyl iodides. Total syntheses of (±) -prezizanol and (±)-prezizaene

1987 ◽  
Vol 28 (43) ◽  
pp. 5075-5078 ◽  
Author(s):  
Edward Piers ◽  
Michel Jean ◽  
Peter S. Marrs
Keyword(s):  
Total Syntheses ◽  
Palladium Catalyzed ◽  
Vinyl Iodides

Stereospecific, Palladium-catalyzed C(sp3)–H Alkenylation and Alkynylation of a Proline Derivative Enabled by 8-Aminoquinoline as a Directing Group

2020 ◽  
Author(s):  
Aleksandra Balliu ◽  
Aaltje Roelofje Femmigje Strijker ◽  
Michael Oschmann ◽  
Monireh Pourghasemi Lati ◽  
Oscar Verho
Keyword(s):  
Carboxylic Acid ◽  
Building Blocks ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
High Yields ◽  
Vinyl Iodides ◽  
Initial Results

<p>In this preprint, we present our initial results concerning a stereospecific Pd-catalyzed protocol for the C3 alkenylation and alkynylation of a proline derivative carrying the well utilized 8‑aminoquinoline directing group. Efficient C–H alkenylation was achieved with a wide range of vinyl iodides bearing different aliphatic, aromatic and heteroaromatic substituents, to furnish the corresponding C3 alkenylated products in good to high yields. In addition, we were able show that this protocol can also be used to install an alkynyl group into the pyrrolidine scaffold, when a TIPS-protected alkynyl bromide was used as the reaction partner. Furthermore, two different methods for the removal of the 8-aminoquinoline auxiliary are reported, which can enable access to both <i>cis</i>- and <i>trans</i>-configured carboxylic acid building blocks from the C–H alkenylation products.</p>

Formal Total Syntheses of Crocacin A-D

2005 ◽  
Vol 70 (10) ◽  
pp. 1696-1708 ◽  
Author(s):  
Magnus Besev ◽  
Christof Brehm ◽  
Alois Fürstner
Keyword(s):  
Natural Products ◽  
Aldol Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Total Syntheses ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
The Common ◽  
Selective Addition

A concise route to the common polyketide fragment5of crocacin A-D (1-4) is presented which has previously been converted into all members of this fungicidal and cytotoxic family of dipeptidic natural products by various means. Our synthesis features asyn-selective titanium aldol reaction controlled by a valinol-derived auxiliary, a zinc-mediated, palladium-catalyzedanti-selective addition of propargyl mesylate10to the chiral aldehyde9, as well as a comparison of palladium-catalyzed Stille and Suzuki cross-coupling reactions for the formation of the diene moiety of the target.

Total Syntheses of Enokipodins A and B Utilizing Palladium-Catalyzed Addition of An Arylboronic Acid to An Allene

2009 ◽  
Vol 11 (6) ◽  
pp. 1441-1443 ◽  
Author(s):  
Masahiro Yoshida ◽  
Yasunobu Shoji ◽  
Kozo Shishido
Keyword(s):  
Arylboronic Acid ◽  
Total Syntheses ◽  
Palladium Catalyzed

Total Syntheses of Prothracarcin and Tomaymycin by Use of Palladium Catalyzed Carbonylation

Tetrahedron ◽  
1986 ◽  
Vol 42 (14) ◽  
pp. 3793-3806 ◽  
Author(s):  
Miwako Mori ◽  
Yasuhiro Uozumi ◽  
Masaya Kimura ◽  
Yoshio Ban
Keyword(s):  
Total Syntheses ◽  
Palladium Catalyzed

Enantioselective Total Syntheses of Lyconadins A–E through a Palladium‐Catalyzed Heck‐Type Reaction

2020 ◽  
Vol 59 (7) ◽  
pp. 2860-2866 ◽  
Author(s):  
Jiayang Zhang ◽  
Yangtian Yan ◽  
Rong Hu ◽  
Ting Li ◽  
Wen‐Ju Bai ◽  
...  
Keyword(s):  
Total Syntheses ◽  
Type Reaction ◽  
Palladium Catalyzed

Enantioselective Total Syntheses of Lyconadins A–E through a Palladium‐Catalyzed Heck‐Type Reaction

2020 ◽  
Vol 132 (7) ◽  
pp. 2882-2888 ◽  
Author(s):  
Jiayang Zhang ◽  
Yangtian Yan ◽  
Rong Hu ◽  
Ting Li ◽  
Wen‐Ju Bai ◽  
...  
Keyword(s):  
Total Syntheses ◽  
Type Reaction ◽  
Palladium Catalyzed
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