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• W2113423614 endingPage "1124" @default.
• W2113423614 startingPage "1113" @default.
• W2113423614 abstract "A chiral approach to (–)-pumiliotoxin C based on an aqueous intramolecular acylnitroso Diels–Alder reaction is described. Upon treatment of the (S)-1,3-diene hydroxamic acid 19, available from L-malic acid, with Pr4NIO4 under the aqueous conditions, the in situ generated acylnitroso compound 19 was subjected to intramolecular [4 + 2] cycloaddition to yield the trans-1,2-oxazino lactam 21 with significantly increased diastereoselectivity in comparison with the same cycloaddition conducted in a chloroform solution. Subsequent addition of the propyl side chain was achieved by means of a tandem Grignard reaction–NaBH3CN reduction in a completely stereocontrolled manner. The bicyclic 1,2-oxazine 26 thus obtained was converted into the all-cis-decahydroquinoline 34 by sequential reductive N–O bond cleavage, aldol condensation of the diketone 31 and hydrogenation of the octahydroquinolone 33. Clemmensen reduction of 34, followed by LiAlH4 reduction, provided a ca. 2 : 1 epimeric mixture of α-methyl and β-methyl isomers 36 and 37, and subsequent debenzylation converted the major isomer 36 into 5-epi-pumiliotoxin C 2. On the other hand, 34 underwent LiAlH4 reduction followed by Swern oxidation to afford a 1.2 : 1 epimeric mixture of the decahydroquinolones 39 and 41. Equilibrium control of this epimeric mixture by prolonged heating with Zn(OTf)2 followed by treatment with ethane-1,2-dithiol resulted in the exclusive formation of the thermodynamically more stable β-methyl epimer 43 as a single isomer, which was converted into (–)-pumiliotoxin C 1 by desulfurization and debenzylation." @default.
• W2113423614 created "2016-06-24" @default.
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• W2113423614 creator A5013478282 @default.
• W2113423614 creator A5046771054 @default.
• W2113423614 date "1996-01-01" @default.
• W2113423614 modified "2023-10-14" @default.
• W2113423614 title "Stereoselective total synthesis of (–)-pumiliotoxin C by an aqueous intramolecular acylnitroso Diels–Alder approach" @default.
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• W2113423614 doi "https://doi.org/10.1039/p19960001113" @default.
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