Stereoselective synthesis of the indolizidine core of the allopumiliotoxins
β Scribed by Choon-Hong Tan; Thomas Stork; Neil Feeder; Andrew B. Holmes
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 218 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
The common indolizidine core leading to the allopumiliotoxins was synthesized using an intramolecular (Z)-N-4-alkenylnitrone cycloaddition reaction as the key step. The synthesis began with (R)-tert-butyl-3-hydroxypent-4-enoate which was obtained via enzymatic resolution using Amano PS lipase.
π SIMILAR VOLUMES
A stereoselective synthesis of the decahydrofluorene core of the hirsutellones was accomplished in eight steps and in 43% overall yield. The key step of the synthesis is the highly stereoselective intramolecular Diels-Alder cyclization of the siloxacyclopentene-constrained tetraene 1.
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