Chemical conversion of humulene to cyclohumulanoids along the biosynthetic pathway. Sterpurene, a hydrocarbon from silver-leaf disease fungus
✍ Scribed by Yoshihiko Murata; Toshikazu Ohtsuka; Haruhisa Shirahama; Takeshi Matsumoto
- Publisher
- Elsevier Science
- Year
- 1981
- Tongue
- French
- Weight
- 136 KB
- Volume
- 22
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Sterpurene, a cyclohumulanoid obtained from silver-leaf disease fungus, was chemically derived from humulene via a route analogous to biosynthesis. Sterpurene (:)l) is a precursory hydrocarbon of oxygenated metabolites 2) of the silver leaf disease fungus, Streum purpureum. Chemistry of the products from this fungus has intensively studied by Ayer and his coworkers. Biosynthetic studies3) indicated that the sterpurene was derived from humulene via protoilludyl cation (2) (Scheme 1). We wish to report here a chemical conversion of humulene to sterpurene along the biosynthetic pathway. 4) Humulene was converted to a cyclooctenol 2 5, through treatment with Hg(N03)26) followed by Li-EtNH2. shown5) Reaction path forming a bridged compound?