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Formal Synthesis of Dictyostatin and Synthesis of Two Dictyostatin Analogues
Author(s) -
Gallon Julien,
Esteban Jorge,
Bouzbouz Samir,
Campbell Matthew,
Reymond Sébastien,
Cossy Janine
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201201001
Subject(s) - stereocenter , stereoselectivity , alkylation , aldehyde , iodide , stereochemistry , convergent synthesis , chemistry , combinatorial chemistry , catalysis , enantioselective synthesis , organic chemistry
A formal convergent synthesis of dictyostatin from ( R )‐Roche ester is described. Synthetic highlights include a Ni‐catalyzed Nozaki–Hiyama–Kishi coupling between an aldehyde and a Z vinyl iodide to assemble the two main fragments, a diastereoselective Myers alkylation, a stereoselective Evans aldolization, two asymmetric Duthaler crotyltitanations, and a stereoselective Pd‐catalyzed Marshall allenylindium addition to install the stereogenic centers of dictyostatin. The synthesis of (9 R )‐ epi ‐dictyostatin and a new ring‐contracted dictyostatin isomer were also achieved.