Photocyclization of Enamides. XXVIII. : A Formal Total Synthesis of (±)-Deserpidine

Naito, Takeaki; Hirata, Y.; Miyata, Okiko; Ninomiya, Ichiya; Inoue, Masatoshi; Kamiichi, Katsuhisa; Doi, Mitsunobu

doi:10.1248/cpb.37.901

Cited by 15 publications

(6 citation statements)

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“…The generality of this synthetic methodology including enamide photocyclization was beautifully provided by another synthesis of deserpidine (6), which has an additional methoxy group in the 18 position. Total synthesis of deserpidine was quite similarly achieved just by adding steps for the introduction of an additional methoxy group at the 18 position to the synthetic intermediate A of yohimbine as shown in Scheme 8.…”

Section: Recent Progress In the Synthesis Of Indole Alkaloids1mentioning

confidence: 97%

Recent Progress in the Synthesis of Indole Alkaloids

Ninomiya¹

1992

J. Nat. Prod.

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Section: Recent Progress In the Synthesis Of Indole Alkaloids1mentioning

confidence: 97%

Recent Progress in the Synthesis of Indole Alkaloids

Ninomiya¹

1992

J. Nat. Prod.

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“…8,9) The generality of this synthetic methodology for indole alkaloids including reductive photocyclization was elegantly confirmed by another synthesis of (Ϯ)-deserpidine which was achieved simply by adding steps for the introduction of an additional oxygen function at the 18-position and for epimerization at the 3-position. 10,11) …”

Section: Synthesis Of Yohimbine Alkaloidsmentioning

confidence: 99%

Development of New Synthetic Reactions for Nitrogen-Containing Compounds and Their Application

Naito

2008

Chem. Pharm. Bull.

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Nitrogen-containing compounds are core parts not only of natural and synthetic medicines but also of biologically active compounds including natural products. This review focuses on the development of new synthetic reactions for nitrogen-containing compounds via three methodologies: the reductive photocycloaddition reaction of enamides, radical addition reaction, and nucleophilic addition reaction. Newly developed reactions were successfully applied to the synthesis of various types of nitrogen-containing compounds including medicines, lead compounds to new drugs, natural alkaloids, and others.

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“…This approach is continuation of our previously established reductive photocyclization of enamides methodology; we have reported efficient synthesis of various natural alkaloids using this method [22,23]. We wanted to further explore this protocol towards the synthesis of structurally more complicated and medicinal important natural alkaloid, (±)reserpine.…”

Section: Introductionmentioning

confidence: 99%