Total Synthesis of Berkeleyamide A and its 10‐epi Isomer

Abstract

A short and efficient synthesis of the novel cytotoxic natural product berkeleyamide A, isolated from a deep‐water Penicillium rubrum, has been accomplished. L‐Leucinol was used as the only chiral starting material. A diastereoselective aldol condensation is the key step in the synthesis.

Tandem-catalysis-enabled highly chemoselective deoxygenative alkynylation and alkylation of tertiary amides: a versatile entry to functionalized α-substituted amines

“…It is worth noting that lactam ( S )- 6 served as an intermediate in Brimble's first enantioselective total synthesis 27 a of the Caspase 1 inhibitor (−)-berkeleyamide A ( 7 ). 27,28…”

Multicomponent Reactions of Phosphines, Enynedioates and Cinnamaldimines Give γ‐Lactams with a 1,3,5‐Hexatriene Moiety for Facile 6π Electrocyclization: Access to Oxindoles, Isatins and Isoxazolinones

“…32 Isoxazolinones, normally synthesized by reduction of methyl ortho ‐nitrobenzoate with zinc and NH 4 Cl33 or photolysis of ortho ‐azidobenzoic acid,34 possess anticonvulsant, antimicrobial and antileukemic activities 35. Last, the tosyl group (Ts) of oxindole 5a can be removed with sodium naphthalenide36 to give only 10% yield of 8a . However, 8a was formed in 91% yield under treatment with neat H 2 SO 4 at room temperature; deprotected isatin 6a′ and isoxazolinone 7a′ can also be obtained by treatment of concentrated H 2 SO 4 , respectively (Scheme c) 37…”