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Total synthesis of ...
Total synthesis of (+)-alexine by utilizing a highly stereoselective 3+2 annulation reaction of an N-tosyl-alpha-amino aldehyde and a 1,3-bis(silyl)propene
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Dressel, Martina (författare)
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Restorp, Per (författare)
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- Somfai, Peter (författare)
- KTH,Organisk kemi
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(creator_code:org_t)
- Wiley, 2008
- 2008
- Engelska.
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Ingår i: Chemistry - A European Journal. - : Wiley. - 0947-6539 .- 1521-3765. ; 14:10, s. 3072-3077
- Relaterad länk:
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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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- A novel route towards the polyhydroxylated pyrrolizidine alkaloid (+)-alexine has been developed. A key step in this synthesis is a highly stereoselective [3+2] annulation reaction of N-Ts-alpha-amino aldehyde 7a (Ts=tosyl) and 1,3-bis(silyl)propene 8a for the construction of the polyhydroxylated pyrrolidine subunit of the target molecule. Previous synthetic strategies rely on carbohydrates that require several protecting-group manipulations, thereby making the total number of steps relatively high. The [3+2] annulation strategy compares favorably with carbohydrate-based syntheses and constitutes a highly efficient entry to polyhydroxylated alkaloids.
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