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Total Synthesis of (−)‐Rhizopodin
Author(s) -
Dalby Stephen M.,
GoodwinTindall Jake,
Paterson Ian
Publication year - 2013
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.201301978
Subject(s) - computer science , modular design , aldol reaction , total synthesis , core (optical fiber) , modularity (biology) , monomer , chemistry , combinatorial chemistry , stereochemistry , programming language , biology , biochemistry , organic chemistry , catalysis , telecommunications , polymer , genetics
Core assembly : The total synthesis of the myxobacterial metabolite rhizopodin, a potent actin‐binding anticancer agent, has been achieved. The modular synthesis utilizes a common C1–C22 monomeric unit to assemble the dimeric 38‐membered macrodiolide core, which was elaborated by a bidirectional boron‐mediated aldol reaction to install the characteristic side‐chains. The final global deprotection was critically dependent on the correct choice of silyl protecting groups at C16/C16′.