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Enantioselective Synthesis of Caprolactam and Enone Precursors to the Heterocyclic DEFG Ring System of Zoanthenol
Author(s) -
Bagdanoff Jeffrey T.,
Behenna Douglas C.,
Stockdill Jennifer L.,
Stoltz Brian M.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600223
Subject(s) - synthon , enantioselective synthesis , enone , alkyne , chemistry , caprolactam , ring (chemistry) , organic chemistry , combinatorial chemistry , catalysis
The enantioselective synthesis of both caprolactam and enone synthons for the DEFG ring system of zoanthenol are described. The evolution of this approach proceeds first through a synthesis using the chiral pool as a starting point. Challenges in protecting‐group strategy led to the modification of this approach beginning with (±)‐glycidol. Ultimately, an efficient approach was developed by employing an asymmetric hetero‐Diels–Alder reaction. The caprolactam building block can be converted by an interesting selective Grignard addition into the corresponding enone synthon. Addition of a model alkyne provides support for the late‐stage addition of a hindered alkyne to the caprolactam building block.