Synthesis of HKI 0231B |
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Authors: | Scopton Alex Kelly T Ross |
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Institution: | E. F. Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA. |
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Abstract: | reaction: see text] The total synthesis of HKI 0231B (1b) was completed in 12 linear steps and 15.6% overall yield. An unusual anionic cyclization provided access to intermediate 61 and the embedded benzcd]indol-3-(1H)-one ring system 3. Directed ortho-lithiation in the presence of a ketone followed by formylation and finally acid-catalyzed methanolysis complete the synthesis. Studies directed toward the construction and reactivity of the lactam acetal functionality present in HKI 0231A (1a) are also reported. |
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