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A new synthesis of tricyclic sesquiterpene (±)-sterpurene
✍ Scribed by Goverdhan Mehta; K. Sreenivas
- Book ID
- 104232265
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 93 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A new synthesis of tricyclic sesquiterpene, sterpurene 1 is reported. An intermolecular [2+2]-photocycloaddition 1415 serves as a key step, which is promoted through the stabilisation of the enone excited state through a b-carbomethoxy substituent on the a,b-unsaturated enone moiety. A tricyclo[6.3.0.0 3,6 ]undecane based advanced intermediate 19 en route to 1, has been fragmented to the bicyclo[6.3.0]undecane system 27 present in the asteriscane-type sesquiterpenoids.
📜 SIMILAR VOLUMES
The cycloadduct (5), which is conveniently prepared by irradiation of ( ), is converted via a I-step sequence, into the