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- W2900645412 abstract "The formal synthesis of (–)‐PHTX is described. Our approach was based on the anodic cyanation of ( S )‐1‐(1‐phenylethyl)‐piperidine (–)‐ 1 to afford α‐aminonitrile 2 in 85 % yield in a 53:47 dr . The presence of the α‐phenylethyl group as the chiral auxiliary ensured the control of the absolute configuration of the future C6 spiro‐center during the alkylation step of 2 , which was carried out with 1‐bromo‐4‐chlorobutane. Next, elaboration of the 1‐azaspiro[5,5]undecane‐7‐one ring system was achieved in a two‐step sequence, involving (a) a Thorpe‐Ziegler annulation, and (b) the hydrolysis–decarboxylation of enaminonitrile (–)‐ 5 to afford spiroketone (+)‐ 6 in >99:1 dr . Finally, the incorporation of the future C7 butyl chain was carried out stereoselectively through a new reaction sequence which involved the synthesis of tricyclic oxazolidinone (–)‐ 11 and alkylation of the intermediary syn ‐fluorohydrin (+)‐ 13 with n BuMgCl to form oxazolidinone (+)‐ 15 in an overall 19 % yield from (–)‐ 1 ." @default.
- W2900645412 created "2018-11-29" @default.
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- W2900645412 date "2018-12-10" @default.
- W2900645412 modified "2023-09-26" @default.
- W2900645412 title "Formal Synthesis of (-)-Perhydrohistrionicotoxin Using a Thorpe-Ziegler Cyclization Approach. Synthesis of Functionalized Aza-Spirocycles" @default.
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- W2900645412 doi "https://doi.org/10.1002/ejoc.201801604" @default.
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