✦ LIBER ✦
Model studies for the stereoselective construction of the BC-ring of armatol F based on Ireland-Claisen rearrangement and relay ring-closing olefin metathesis
✍ Scribed by Kenshu Fujiwara; Keita Tanaka; Yasushi Katagiri; Hidetoshi Kawai; Takanori Suzuki
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- French
- Weight
- 580 KB
- Volume
- 51
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
Armatol F, isolated from the red alga Chondria armata as a polyether triterpene, has a fused tricyclic ether moiety (BCD-ring) with an unusual cis ring junction at C18-C19 between the C-and D-rings. En route to the total synthesis of armatol F, the stereoselective construction of the C18 and C19 stereocenters by Ireland-Claisen rearrangement and the formation of the C-ring by relay ring-closing olefin metathesis were established through the synthesis of monocyclic (C-ring) and bicyclic (BC-ring) model compounds.