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Total Synthesis of Myceliothermophins C, D, and E
Author(s) -
Nicolaou K. C.,
Shi Lei,
Lu Min,
Pattanayak Manas R.,
Shah Akshay A.,
Ioannidou Heraklidia A.,
Lamani Manjunath
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201406815
Subject(s) - total synthesis , stereochemistry , enantiomer , chemistry , cascade , decalin , stereocenter , enantioselective synthesis , organic chemistry , chromatography , catalysis
The total synthesis of cytotoxic polyketides myceliothermophins E ( 1 ), C ( 2 ), and D ( 3 ) through a cascade‐based cyclization to form the trans‐fused decalin system is described. The convergent synthesis delivered all three natural products through late‐stage divergence and facilitated unambiguous C21 structural assignments for 2 and 3 through X‐ray crystallographic analysis, which revealed an interesting dimeric structure between its enantiomeric forms.