Formal Total Synthesis of (+)-Salicylihalamides A and B: A Combined Chiral Pool and RCM Strategy
β Scribed by Yang, KyoungLang; Blackman, Burchelle; Diederich, Wibke; Flaherty, Patrick T.; Mossman, Craig J.; Roy, Subho; Ahn, Yu Mi; Georg, Gunda I.
- Book ID
- 125546702
- Publisher
- American Chemical Society
- Year
- 2003
- Tongue
- English
- Weight
- 203 KB
- Volume
- 68
- Category
- Article
- ISSN
- 0022-3263
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π SIMILAR VOLUMES
## Abstract The paper illustrates two efficient routes to macrolactone **19** containing a 3β(__para__βmethoxybenzyloxy)propyl side chain at Cβ15. The chiral center at Cβ15 was introduced by a Noyori reduction of keto ester **5**. The intermediate common to both routes, aldehyde **8**, was prepared
We have devised a total synthesis of (12R,13S,15R) salicylihalamides A and B, which allowed revision of the absolute stereochemistry of the natural compounds. The same strategy was then applied to the preparation of naturally occurring salicylihalamides.