Preparation of the "Ziegler key intermediate" 2from lactone 3, readily obtained from hydroxy-O-ionone, was studied. In a first exploratory approach, lactones 11 and 13 were obtained but further transformations aimed at setting the ring junction were unsuccessful due to unexpected rearrangements. Thr
A practical and efficient synthesis of the ziegler key intermediate for the synthesis of forskolin
✍ Scribed by Maria I Colombo; Carmen Somoza; Juan Zinczuk; José A Bacigaluppo; Edmundo A Rúveda
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- French
- Weight
- 249 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The Ziegler intermediate 2, previously used in three total syntheses of forskolin (1) has been synthesized efficiently from enone 3. The key transformation of this sequence is the early and stereoselective introduction of the C-6, C-7 oxygen functional groups present in the natural product.
The highly oxygenated labdane diterpene forskolin (l), isolated from the roots of the Indian herb Coleus forskohlii,' has generated an enormous amount of synthetic interest2 because of its unique structural
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A simple route for the enanrioselective synthesis of key intermediates (11 and 12) for the total synthesis of forskolin has been developed starting from acid 6 and (S)-alcohol 5. The latter is prepared by enantioselective catalytic CBS reduction of dienone 3, and is converted by an intramolecular Di
An efficient and practical method for the synthesis of (4R,5R)-4,5-O-isopropylidene-cyclopent-2-enone was developed from D-ribose by using a ring-closing metathesis reaction.
An enantioselective route for the total synthesis of forskolin, a potent activator of adenylate cyclase, has been developed which is based on reduction of dienone 3 to the (S)-alcohol4 and conversion in two steps to tricyclic lactone 9, obtained in optically pure form simply by recrystallization. A