Abstract
In this paper we describe the stereoselective synthesis of functionalized lactam 7 via two enantiospecific piperidine-forming techniques and its employment in a general synthetic approach to Nuphar alkaloids. Specifically, the formation of piperidine 18 by formal [3 + 3] cycloaddition and stepwise annelation processes is described; the latter technique was found to be significantly more efficient than the Pd-catalyzed TMM addition process. Finally, exploitation of the exocyclic alkene installed in the piperidine-forming reaction in the transformation of 18 to (-)-deoxynupharidine ((-)-2), (-)-castoramine ((-)-3), and (-)-nupharolutine ((-)-4) via intermediate lactam 7 is delineated.
| Original language | English |
|---|---|
| Pages (from-to) | 207-213 |
| Number of pages | 7 |
| Journal | Journal of Organic Chemistry |
| Volume | 70 |
| Issue number | 1 |
| Early online date | 2 Dec 2004 |
| DOIs | |
| Publication status | Published - 7 Jan 2005 |
| Externally published | Yes |
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Development of a Flexible Approach to Nuphar Alkaloids via Two Enantiospecific Piperidine-Forming Reactions. / Goodenough, Katharine M.; Moran, Wesley J.; Raubo, Piotr; Harrity, Joseph P.A.
In: Journal of Organic Chemistry, Vol. 70, No. 1, 07.01.2005, p. 207-213.Research output: Contribution to journal › Article
TY - JOUR
T1 - Development of a Flexible Approach to Nuphar Alkaloids via Two Enantiospecific Piperidine-Forming Reactions
AU - Goodenough, Katharine M.
AU - Moran, Wesley J.
AU - Raubo, Piotr
AU - Harrity, Joseph P.A.
PY - 2005/1/7
Y1 - 2005/1/7
N2 - In this paper we describe the stereoselective synthesis of functionalized lactam 7 via two enantiospecific piperidine-forming techniques and its employment in a general synthetic approach to Nuphar alkaloids. Specifically, the formation of piperidine 18 by formal [3 + 3] cycloaddition and stepwise annelation processes is described; the latter technique was found to be significantly more efficient than the Pd-catalyzed TMM addition process. Finally, exploitation of the exocyclic alkene installed in the piperidine-forming reaction in the transformation of 18 to (-)-deoxynupharidine ((-)-2), (-)-castoramine ((-)-3), and (-)-nupharolutine ((-)-4) via intermediate lactam 7 is delineated.
AB - In this paper we describe the stereoselective synthesis of functionalized lactam 7 via two enantiospecific piperidine-forming techniques and its employment in a general synthetic approach to Nuphar alkaloids. Specifically, the formation of piperidine 18 by formal [3 + 3] cycloaddition and stepwise annelation processes is described; the latter technique was found to be significantly more efficient than the Pd-catalyzed TMM addition process. Finally, exploitation of the exocyclic alkene installed in the piperidine-forming reaction in the transformation of 18 to (-)-deoxynupharidine ((-)-2), (-)-castoramine ((-)-3), and (-)-nupharolutine ((-)-4) via intermediate lactam 7 is delineated.
UR - http://www.scopus.com/inward/record.url?scp=11844292757&partnerID=8YFLogxK
U2 - 10.1021/jo048455k
DO - 10.1021/jo048455k
M3 - Article
C2 - 15624924
AN - SCOPUS:11844292757
VL - 70
SP - 207
EP - 213
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 1
ER -