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Total Synthesis of the Spermidine Alkaloid 13-Hydroxyisocyclocelabenzine

✍ Scribed by Yi Li; Anthony Linden; Manfred Hesse

Publisher
John Wiley and Sons
Year
2003
Tongue
German
Weight
168 KB
Volume
86
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A convergent total synthesis of 13‐hydroxyisocyclocelabenzine was developed. (3__S__)‐Methyl 3‐amino‐3‐phenylpropanoate (4) was used as the chiral building block. The 3,4‐dihydro‐4‐hydroxyisoquinolin‐1(2__H__)‐one derivative (5), the key fragment for the total synthesis, was prepared by a novel base‐catalyzed lactone‐lactam ring enlargement (Scheme 3). The resulting target C(13) epimers 3a/3b from macrocyclization (Scheme 4) were separated by repeated flash chromatography. The absolute configuration of the synthetic alkaloid was determined by an X‐ray crystal‐structure analysis, which enabled us to determine the absolute configuration (9__S__,13__R__) for natural 3a with positive [α]~D~.

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