Sökning: id:"swepub:oai:DiVA.org:uu-84527" >
Syntheses of (±)-α-...
Syntheses of (±)-α- and (±)- γ- Lycorane via a Stereocontrolled Organopalladium Route
-
- Bäckvall, Jan-Erling (författare)
- Uppsala universitet,Avdelningen för organisk kemi
-
- Andersson, Pher (författare)
- Uppsala universitet,Avdelningen för organisk kemi
-
- Stone, Guy (författare)
- Uppsala universitet,Avdelningen för organisk kemi
-
visa fler...
-
- Gogoll, Adolf (författare)
- Uppsala universitet,Avdelningen för organisk kemi
-
visa färre...
-
(creator_code:org_t)
- 2002-05-01
- 1991
- Engelska.
-
Ingår i: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 56:9, s. 2988-2993
- Relaterad länk:
-
https://urn.kb.se/re...
-
visa fler...
-
https://doi.org/10.1...
-
visa färre...
Abstract
Ämnesord
Stäng
- Total syntheses of (+/-)-alpha-and (+/-)-gamma-lycorane are described. The key steps in the syntheses are the stereocontrolled palladium-catalyzed intramolecular 1,4-chloroamidation of 12 to 13 and the subsequent anti-stereoselective copper-catalyzed S(N)2' reaction of allylic chloride 13 with [3,4-(methylenedioxy)phenyl]magnesium bromide to give 14. Hexahydroindole 14 has the required relative stereochemistry between carbons 3a, 7, and 7a for alpha-lycorane (1a) and was transformed to the latter via 15 and 16. The epimeric gamma-lycorane (2) was obtained by performing the Bischler-Napieralski cyclization on 14, which led to a highly stereoselective isomerization to give exclusively 17. Compound 17 was subsequently transformed to 2. The overall yield from ester 8 to (+/-)-alpha- and (+/-)-gamma-lycorane was 40 and 36%, respectively.
Ämnesord
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Nyckelord
- Organic chemistry
- Organisk kemi
Publikations- och innehållstyp
- ref (ämneskategori)
- art (ämneskategori)
Hitta via bibliotek
Till lärosätets databas