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Enantioselective Synthesis of the [6,6] Spiroketal Core of Reveromycin A
β Scribed by Drouet, Keith E.; Ling, Taotao; Tran, Hung V.; Theodorakis, Emmanuel A.
- Book ID
- 127320987
- Publisher
- American Chemical Society
- Year
- 2000
- Tongue
- English
- Weight
- 92 KB
- Volume
- 2
- Category
- Article
- ISSN
- 1523-7060
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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.
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.