Abstract
The β-amino ester 6 is synthesized via the diastereoselective Michael addition of the lithium amide derived from amine 5 to methyl ( E)-2-hexenoate. This ester is converted to the pyrrolidinone 8 via an aldol condensation/deprotection/cyclization. Transformation of the lactam 8 into thiolactam 11 followed by Eschenmoser sulfide contraction provides (2 S,3 S,4 R)-plakoridine A.
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