Chemical predisposition in synthesis: application to the preparation of the pyrrolidine natural products, plakoridines A and B

Laura L. Etchells; Madeleine Helliwell; Neil M. Kershaw; Ali Sardarian; Roger C. Whitehead

doi:10.1016/j.tet.2006.08.075

Chemical predisposition in synthesis: application to the preparation of the pyrrolidine natural products, plakoridines A and B

Laura L. Etchells, Madeleine Helliwell, Neil M. Kershaw, Ali Sardarian, Roger C. Whitehead

Research output: Contribution to journal › Article › peer-review

Abstract

The pyrrolidine natural products, plakoridines A and B, as well as an array of unnatural analogues, have been prepared using a five-step synthetic sequence modelled on a biogenetic theory. The key transformation involves a 'Mannich/Michael/internal-redox' cascade, which proceeds in yields of 31-63%. © 2006 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	10914-10927
Number of pages	13
Journal	Tetrahedron
Volume	62
Issue number	47
DOIs	https://doi.org/10.1016/j.tet.2006.08.075
Publication status	Published - 20 Nov 2006

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10.1016/j.tet.2006.08.075

CCDC 612879: Experimental Crystal Structure Determination
Etchells, L. L. (Contributor), Helliwell, M. (Contributor), Kershaw, N. M. (Contributor), Sardarian, A. (Contributor) & Whitehead, R. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2006
DOI: 10.5517/ccnkr97, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccnkr97&sid=DataCite
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title = "Chemical predisposition in synthesis: application to the preparation of the pyrrolidine natural products, plakoridines A and B",

abstract = "The pyrrolidine natural products, plakoridines A and B, as well as an array of unnatural analogues, have been prepared using a five-step synthetic sequence modelled on a biogenetic theory. The key transformation involves a 'Mannich/Michael/internal-redox' cascade, which proceeds in yields of 31-63%. {\textcopyright} 2006 Elsevier Ltd. All rights reserved.",

author = "Etchells, {Laura L.} and Madeleine Helliwell and Kershaw, {Neil M.} and Ali Sardarian and Whitehead, {Roger C.}",

year = "2006",

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T1 - Chemical predisposition in synthesis: application to the preparation of the pyrrolidine natural products, plakoridines A and B

AU - Etchells, Laura L.

AU - Helliwell, Madeleine

AU - Kershaw, Neil M.

AU - Sardarian, Ali

AU - Whitehead, Roger C.

PY - 2006/11/20

Y1 - 2006/11/20

N2 - The pyrrolidine natural products, plakoridines A and B, as well as an array of unnatural analogues, have been prepared using a five-step synthetic sequence modelled on a biogenetic theory. The key transformation involves a 'Mannich/Michael/internal-redox' cascade, which proceeds in yields of 31-63%. © 2006 Elsevier Ltd. All rights reserved.

AB - The pyrrolidine natural products, plakoridines A and B, as well as an array of unnatural analogues, have been prepared using a five-step synthetic sequence modelled on a biogenetic theory. The key transformation involves a 'Mannich/Michael/internal-redox' cascade, which proceeds in yields of 31-63%. © 2006 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tet.2006.08.075

DO - 10.1016/j.tet.2006.08.075

M3 - Article

SN - 0040-4020

VL - 62

SP - 10914

EP - 10927

JO - Tetrahedron

JF - Tetrahedron

IS - 47

ER -

Chemical predisposition in synthesis: application to the preparation of the pyrrolidine natural products, plakoridines A and B

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CCDC 612879: Experimental Crystal Structure Determination

Cite this