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A Convergent Strategy for the Pamamycin Macrodiolides: Total Synthesis of Pamamycin‐607, Pamamycin‐593, and Pamamycin‐621D Precursors
Author(s) -
Lanners Steve,
NorouziArasi Hassan,
SalomRoig Xavier J.,
Hanquet Gilles
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200701749
Subject(s) - aldol reaction , tetrahydrofuran , isomerization , total synthesis , chemistry , solvent , stereochemistry , key (lock) , organic chemistry , computer science , catalysis , computer security
A convergent total synthesis of pamamycin‐607 ( 1 ), isolated from Streptomyces alboniger , was achieved by an E – Z isomerization of a tetrahydrofuran alkylidene and a regio‐ and diastereoselective solvent‐dependent cyclo ‐C 6 H 11 BCl/Et 3 N‐mediated aldol reaction as the key steps. The second key step was extended to other ketones, opening the route to new pamamycin macrodiolides, for example, pamamycin‐593 and pamamycin‐621D.