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A total synthesis of magallanesine via [1, 2]-Meisenheimer rearrangement

✍ Scribed by Ryuji Yoneda; Yasuhiko Sakamoto; Yoshifumi Oketo; Kayoko Minami; Shinya Harusawa; Takushi Kurihara

Book ID: 104214314
Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 257 KB
Volume: 35
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)73089-9

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✦ Synopsis

A straightforward synthesis of magallanesine 1 from azetoisoquinoline 4 has been accomplished via [ 1.21~Meisenheimer rearrangement and an intramolecular Heck cyclization as the key reactions. Members of the plant family Berberidaceae have long been known to contain a number of alkaloids, and recently the first example of a new class of isoindolobenzaxocine alkaloid, magallanesine 1, was isolated from Berberis Darwinii Hook, collected in southern Chile.l*2 The only total synthesis, in 1989, was reported by

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