Asymmetric Synthesis of the Functionalized A/E-Ring Fragment of C18-Diterpenoid Alkaloids

Asymmetric Synthesis of the Functionalized A/E-Ring Fragment of C18-Diterpenoid Alkaloids

A new asymmetric synthesis of the A/E-ring fragment of C18-diterpenoid alkaloids is described. The crucial contiguous stereogenic centers at C4, C5, and C11 were established through an asymmetric Michael addition/allylation sequence. The unique azabicyclo[3.3.1]­nonane motif (A/E rings) was assemble...

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Veröffentlicht in:Journal of organic chemistry 2024-02, Vol.89 (4), p.2807-2811
Hauptverfasser: Lu, Fei, Shao, Yu, Yan, Shulin, Yang, Dingyi, Song, Hao, Zhang, Dan, Liu, Xiao-Yu, Qin, Yong
Format: Artikel
Sprache:eng
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Zusammenfassung:A new asymmetric synthesis of the A/E-ring fragment of C18-diterpenoid alkaloids is described. The crucial contiguous stereogenic centers at C4, C5, and C11 were established through an asymmetric Michael addition/allylation sequence. The unique azabicyclo[3.3.1]­nonane motif (A/E rings) was assembled by employing ring-closing metathesis and Mitsunobu reaction as key strategies.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02745