Synthetic studies on reveromycin A: Stereoselective synthesis of the spiroketal system
β Scribed by Takeshi Shimizu; Ryoichi Kobayashi; Katsuhisa Osako; Hiroyuki Osada; Ta-i Nakata
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- French
- Weight
- 228 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
The 6,6-spiroketal system of reveromycin A (1), corresponding to the C9-C20 part, was Slm'eoseleetively synthesized and the absolute configuration at Cll, C12, C15, C18 and C19 of I was confirmed by the synthesis of the 5,6-spiroketal derivative degradated from 1.
π SIMILAR VOLUMES
The asymmetric synthesis of the 6,6-spiroketal fragment 15 of the epidermal growth factor inhibitor reveromycin A (1) is described. A hetero-Diels-Alder reaction was utilized to construct the 6,6-spiroketal 14 and subsequent stereoselective hydroboration provided reveromycin A spiroketal 15.
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The IJK-ring system of brevetoxin-B was stereoselectively synthesized based on the 6-endo-cyclizations of a hydroxy methylepoxide and a hydroxy styrylepoxide, and the direct introduction of the C-4 unit as the side chain.