Formal synthesis of actinoranone using a one-pot semipinacol rearrangement/Wittig reaction

Here, we report a formal synthesis of the marine cytotoxic meroterpenoid actinoranone. Key steps include a semipinacol rearrangement/Wittig reaction sequence and a chiral pool approach for the syntheses of the tetralone and the ocatalin fragments, respectively. The presented route provides access to...

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Bibliographic Details
Published in:Tetrahedron 2019-01, Vol.75 (1), p.10-16
Main Authors: Menger, Martina, Christmann, Mathias
Format: Article
Language:English
Subjects:
Actinoranone
Chiral pool
Sclareolide
Semipinacol rearrangement
Terpenes
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Summary:Here, we report a formal synthesis of the marine cytotoxic meroterpenoid actinoranone. Key steps include a semipinacol rearrangement/Wittig reaction sequence and a chiral pool approach for the syntheses of the tetralone and the ocatalin fragments, respectively. The presented route provides access to the natural product in 14 steps in the longest linear sequence. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.11.003