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Preparation of cis-...
Preparation of cis-5-methoxy-and-7-methoxy-1-acetoxy-1,2,3,4,4a,10a-hexahydro-9(10H)-phenanthrenone. An epoxide-arene reaction involving a selective 1,2-alkyl shift rearrangement
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- Garg, Neeraj (author)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi
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- Gogoll, Adolf (author)
- Uppsala universitet,Organisk kemi
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Westerlund, C (author)
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Sundell, S (author)
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- Karlen, Anders (author)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi
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- Hallberg, Anders (author)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi
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(creator_code:org_t)
- 1996
- 1996
- English.
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In: Tetrahedron. - 0040-4020 .- 1464-5416. ; 52:48, s. 15209-15224
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
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- The preparation of cis-1α-acetoxy-7-methoxy-1,2,3,4,4a,10a-hexahydro-9(10H)- phenanthrenone 5 was accomplished starting from 6-methoxy-1-tetralone. Reduction of 7-methoxy-1,2,3, 4,9,10-hexahydro-1-oxo-phenanthrene 8, acetylation and subsequent oxidation delivered 5. Application of an analogus procedure to the preparation of cis-1β-acetoxy-5-methoxy-1,2,3,4,,4a,10a-hexahydro-9(10H)- phenanthrenone 6 was not feasible. A more elaborate route was developed for the synthesis of compound 6, where an epoxide-arene reaction involving a 1,2-alkyl shift rearrangement, constituted a highly selective key transformation. The compounds 5 and 6 were prepared. A route was developed for the synthesis of compound 6, where an epoxide-arene reaction involving a 1,2-alkyl shift rearrangement, constituted a highly selective key transformation.
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