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Synthetic Studies Towards the Core Structure of Nakadomarin A by a Thioamide‐Based Strategy
Author(s) -
Chavda Jai K.,
Procopiou Panayiotis A.,
Horton Peter N.,
Coles Simon J.,
Porter Michael J.
Publication year - 2014
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.201301063
Subject(s) - chemistry , thioamide , iminium , stereocenter , nucleophile , furan , ring (chemistry) , allylic rearrangement , allene , heteroatom , coupling reaction , sn2 reaction , stereochemistry , combinatorial chemistry , organic chemistry , ion , enantioselective synthesis , catalysis
The tricyclic BCD substructure of the marine natural product nakadomarin A has been synthesised. The strategy utilised a key carbon–carbon bond‐forming reaction between a furan and an N ‐acyliminium ion derived from a secondary thiolactam. In addition, a novel three‐component coupling reaction between a thioamide, an allylic bromide and an isocyanate, leading to the establishment of two new stereogenic centres, is reported.