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Synthesis of (±)‐Merrilactone A and (±)‐Anislactone A
Author(s) -
Shi Lei,
Meyer Karsten,
Greaney Michael F.
Publication year - 2010
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.201005156
Subject(s) - computer science , center (category theory) , scheme (mathematics) , cleavage (geology) , information retrieval , chemistry , engineering , mathematics , mathematical analysis , geotechnical engineering , fracture (geology) , crystallography
A concise synthesis of each of the sesquiterpenoids merrilactone A and anislactone A is described using a common route. Reductive cleavage of an epoxide using Ti III and radical cyclization is used to install the C9 quaternary center at the heart of the BC bicycle (see scheme). Selective lactonization sequences then define regiodivergent pathways to both merrilactone A (formal synthesis) and anislactone A (total synthesis).