Premium
Synthesis of an Advanced Maoecrystal V Core Structure
Author(s) -
Dong Lin,
Deng Lujiang,
Lim Yee Hwee,
Leung Gulice Y. C.,
Chen David Y.K.
Publication year - 2011
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.201100232
Subject(s) - intramolecular force , cyclopropanation , chemistry , stereochemistry , core (optical fiber) , cleavage (geology) , sequence (biology) , key (lock) , combinatorial chemistry , computer science , organic chemistry , catalysis , biology , paleontology , telecommunications , biochemistry , computer security , fracture (geology)
Get to the core : The synthesis of an advanced structure of the recently reported cytotoxic diterpenoid maoecrystal V ( 1 ) has been accomplished. The key carbon–carbon bond‐forming events feature an intramolecular Diels–Alder reaction, a cyclopropanation/reductive cleavage sequence, and an intramolecular alkylative lactonization reaction. Furthermore, a hydroxyl‐directed hydrogenation was implemented to cast the desired C5 stereochemistry.