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Diterpenoid total synthesis, XXIX. Synthesis of (±)‐14‐deoxystypoldione, an analogue of the marine natural product stypoldione
Author(s) -
Mori Kenji,
Koga Yasuo
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1991199101132
Subject(s) - chemistry , moiety , natural product , total synthesis , stereochemistry , terpenoid , intramolecular force , metabolite , organic chemistry , biochemistry
(±)‐14‐Deoxystypoldione ( 2 ) has been synthesized by starting from geranylacetone. The key step was the construction of the spirobenzofuran moiety by an intramolecular Michael addition ( 15 → 16 ). (−)‐Stypoldione is the ichthyotoxic and cytotoxic metabolite of the tropical brown alga Stypopodium zonale (Lamouroux) Papenfuss.