The Journal of organic chemistry

Formal Synthesis of (+)-and (-)-Perhydrohistrionicotoxin: A “Double Henry”/Enzymatic Desymmetrization Route to the Kishi Lactam1

FA Luzzio, RW Fitch

文献索引：Luzzio, Frederick A.; Fitch, Richard W. Journal of Organic Chemistry, 1999 , vol. 64, # 15 p. 5485 - 5493

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被引用次数: 43

摘要

Both antipodes of the Kishi lactam (3), the versatile intermediate for the synthesis of the perhydrohistrionicotoxin (pHTX) alkaloids, have been prepared. The synthetic route involved a “double Henry” condensation between glutaraldehyde and nitroacetal 5 giving meso dioxanyldiol 4 which was acetylated and reduced to afford meso dioxane amide 8. Ultrasound-promoted deacetalization of 8 followed by Wittig olefination and reduction ...