Total Synthesis of Hirsutellone B
✍ Scribed by K. C. Nicolaou; David Sarlah; T. Robert Wu; Weiqiang Zhan
- Publisher
- John Wiley and Sons
- Year
- 2009
- Tongue
- English
- Weight
- 369 KB
- Volume
- 121
- Category
- Article
- ISSN
- 0044-8249
No coin nor oath required. For personal study only.
✦ Synopsis
Hirsutellones, [1] pyrrospirones, [2] and pyrrocidines [3] belong to a growing class of fungal secondary metabolites whose biological properties include antifungal and antibiotic activities.
📜 SIMILAR VOLUMES
A strategy of tandem ketene-trapping/IMDA toward the total synthesis of the hirsutellones was attempted. The AB ring moiety of the hirsutellones was constructed with the proper stereochemistry.
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.