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Syntheses of 7α- and 7β-protoilludanol, and 7(13)-protoilludene, possible biogenetic intermediates for illudoid sesquiterpenes

✍ Scribed by Yasufumi Ohfune; Haruhisa Shirahama; Takeshi Matsumoto


Publisher
Elsevier Science
Year
1975
Tongue
French
Weight
251 KB
Volume
16
Category
Article
ISSN
0040-4039

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✦ Synopsis


Several groups suggested1 that the cis-anti-cis protoilludanyl cation 2_ was a key intermediate in the conversion of humulene into illudoids*. Recent studies


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✍ Harapanhalli, Ravi S. 📂 Article 📅 1988 🏛 John Wiley and Sons 🌐 English ⚖ 383 KB

A seven-step synthesis of a new intermediate (5a,fa,llfi)-3,6dioxogermacr-l-cn-l3,7-olide (10) is describcd starting from [ -)-~-santonin (I). The key stcp in thc transformation was photolytic skclctal rearrangement of (4qSP,601,11 F)-S-hydroxy-2oxoeudesman-l3.6-olide (9) to the W e compound, scnsit