We have recently communicated our results on a novel strategy to etficiently and stereoselectively construct the quassinoid framework via a Diene-Transmissive Diels-Alder strategy (Eq l).l Although both the hetero-and intramolecular Diels-Alders proceeded with complete endo-selectivity, the stereoch
Synthesis of an advanced forskolin intermediate
β Scribed by Stefan Bick; Silke Zimmermann; Heike Meuer; William S. Sheldrick; Peter Welzel
- Publisher
- Elsevier Science
- Year
- 1993
- Tongue
- French
- Weight
- 860 KB
- Volume
- 49
- Category
- Article
- ISSN
- 0040-4020
No coin nor oath required. For personal study only.
π SIMILAR VOLUMES
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
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