Hetero-Diels–Alder synthesis of the spiroketal fragment of reveromycin A
✍ Scribed by Mariana El Sous; Mark A Rizzacasa
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 132 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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.
📜 SIMILAR VOLUMES
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.
The hetero-Diels-Alder reaction between 1,3-dimethoxy-1-trimethylsilyloxybutadlene 4, and cinnamaldehyde 5, produces (+) kawain in 75% and 84% yield respectively when catalyzed by Eu(fod)g or Yb(fod)g. When Ag(fod) is employed as the catalyst a unique condensation reaction occurs which produces two