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Total Synthesis of (±)-Clavizepine by Hiroyuki Ishibashi; Kazutaka Takagaki; Noriko Imada; Masazumi Ikeda is a Chemistry article available to read on EtoBox.

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Absfmcl: The fmt total synthuis of benmpyraoobenzazepine alkaloid (f)-clavizepiie (1) has been achieved by usiag Ihe Bradsher cycliition of the keto ester 16 (leading to 18) and the Pummenx-type cyclization of the sulfoxide 25 (leading to 26) as the key \*PL (-)-Clavizepine (1) is an alkaloid isolated in 1986 from Corydulis claviculutu (L.) DC.1 The structure of 1 was assigned through examination of its UV, tH and 13C NMR, and mass spectral characteristics. The gross structure of 1 reveals a unique I-benzopyrano3-benrazepine skeleton bearing one asymmetric center (Cl&, though its absolute contlguration is unknown. Another intriguing feature is the presence of a pharmacologically attractive I-aryl3benzazepine moiety2 as the structural subunit. Prom a biogenetic point of view, this alkaloid has been suggested to be the result of a rearrangement of the cularine system 2.3 In this paper, we present the details of our work on the first total synthesis of (f)-clavizepine.4\*'5 While a variety of possible strategies for the assembly of this alkaloid could be envisioned on the basis of a retrosynthetic analysis, we decided to employ our method of constructing the 3-benzazepine skeleton, wh

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Author

Hiroyuki Ishibashi; Kazutaka Takagaki; Noriko Imada; Masazumi Ikeda

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

1994

Language

EN

Field

Chemistry (Physical Sciences)