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

Takeaki NAITO; Yumiko HIRATA; Okiko MIYATA; Ichiya NINOMIYA; Masatoshi INOUE; Katsuhisa KAMIICHI; Mitsunobu DOI

doi:10.1248/cpb.37.901

Chemical and Pharmaceutical Bulletin

Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363

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

Takeaki NAITO, Yumiko HIRATA, Okiko MIYATA, Ichiya NINOMIYA, Masatoshi INOUE, Katsuhisa KAMIICHI, Mitsunobu DOI

Author information

Keywords: deserpidine, total synthesis, yohimbine, reserpine, indole alkaloid, photocyclization, enamide, epoxyketone

JOURNAL FREE ACCESS

1989 Volume 37 Issue 4 Pages 901-906

DOI https://doi.org/10.1248/cpb.37.901

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Abstract

A formal total synthesis of (±)-deserpidine (1) was accomplished by preparing the known synthetic precursors, two hydroxyesters 19 and 20, via a route involving regioselective formation of the 18-methoxyenone 10a followed by regioselective C-acylation of the enone 10a.

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