Development of radical addition–cyclization–elimination reaction of oxime ether and its application to formal synthesis of (±)-martinelline

Radical addition–cyclization–elimination (RACE) reaction of oxime ether carrying unsaturated ester provides a novel method for the construction of pyrroloquinoline. Treatment of oxime ethers with Bu 3SnH and AIBN gave N-norpyrroloquinoline as a major product, which was also obtained by the radical r...

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Bibliographic Details
Published in:Tetrahedron 2007-10, Vol.63 (40), p.10092-10117
Main Authors: Miyata, Okiko, Shirai, Atsushi, Yoshino, Shintaro, Nakabayashi, Toshiki, Takeda, Yoshifumi, Kiguchi, Toshiko, Fukumoto, Daisuke, Ueda, Masafumi, Naito, Takeaki
Format: Article
Language:English
Subjects:
Martinelline
Oxime ether
Pyrroloquinoline
Radical reaction
α,β-unsaturated ester
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Summary:Radical addition–cyclization–elimination (RACE) reaction of oxime ether carrying unsaturated ester provides a novel method for the construction of pyrroloquinoline. Treatment of oxime ethers with Bu 3SnH and AIBN gave N-norpyrroloquinoline as a major product, which was also obtained by the radical reaction of the corresponding hydrazone and imine. The radical reaction of aldehyde and ketone carrying unsaturated ester proceeded stereoselectively to give cis-furoquinolines and cis-hydroxyesters. The RACE reactions by using each of Bu 3SnNMe 2, Bu 3SnD, and/or D 2O were also examined in order to propose a reaction pathway to N-norpyrroloquinoline. Furthermore, the synthetic utility of RACE reaction is demonstrated by preparation of a key intermediate for the synthesis of (±)-martinelline. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2007.07.007