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Synthesis of Functionalized Bicyclo[3.2.1]octan-6-ones for Diterpenoids: Allylsilane Directed Pummerer Reaction: Insertion Reactions of Diazoketones.

✍ Scribed by Philip Magnus; Trevor Rainey; Vince Lynch


Publisher
John Wiley and Sons
Year
2003
Weight
152 KB
Volume
34
Category
Article
ISSN
0931-7597

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Synthesis of functionalized bicyclo[3.2.
✍ Philip Magnus; Trevor Rainey; Vince Lynch πŸ“‚ Article πŸ“… 2003 πŸ› Elsevier Science 🌐 French βš– 144 KB

The sulfide 5 underwent Pummerer cyclization to give 6, whereas the allyl silane analog 10 produced the bicyclo[3.2.1]octanones 11 and 11a. Extension of this methodology to 15 resulted in 16 without the necessity for allyl silane activation. The intermediate diazoketone 14 on treatment with BF 3 β€’OE