Studies Toward an Asymmetric Synthesis of CP-263,114 and CP-225,917

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Title:Studies Toward an Asymmetric Synthesis of CP-263,114 and CP-225,917
Creators:
Devaux, Jean-François
O'Neil, Steven V.
Guillo, Nathalie
Paquette, Leo A.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 4, pp. 490-510
Uncontrolled Keywords:Total synthesis, Claisen rearrangement, Dihydroxylation, Allylic oxidation, Birch reduction, CP compounds, Iodolactonization

Abstract

An enantioselective approach to construction of the complex framework of the CP compounds is presented. The synthesis relies on initial elaboration of the two sidechains. The "upper" appendage was asymmetrically dihydroxylated with both AD-mix reagents in order to lend flexibility to the scheme and provide the necessary handle for evolving the additional stereogenic centers. These fragments were linked to benzoic acid <i>via</i> Birch reduction-alkylation and subsequent cuprate addition. A series of functionalization reactions including dissolving metal reduction, Claisen rearrangement, iodolactonization, regioselective epoxide cleavage-oxidation, and intramolecular Wadsworth-Emmons cyclization took advantage of highly efficient stereocontrol. However, this flexibility was thwarted when deprotonation of a penultimate intermediate failed to be regioselective in the proper direction. <p>

Title:Studies Toward an Asymmetric Synthesis of CP-263,114 and CP-225,917
Creators:
Devaux, Jean-François
O'Neil, Steven V.
Guillo, Nathalie
Paquette, Leo A.
Uncontrolled Keywords:Total synthesis, Claisen rearrangement, Dihydroxylation, Allylic oxidation, Birch reduction, CP compounds, Iodolactonization
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:65
Number:4
Page Range:pp. 490-510
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20000490UNSPECIFIED
ID Code:1656
Item Type:Article
Deposited On:06 Feb 2009 17:11
Last Modified:06 Feb 2009 16:11

Citation

Devaux, Jean-François; O'Neil, Steven V.; Guillo, Nathalie; Paquette, Leo A. (2000) Studies Toward an Asymmetric Synthesis of CP-263,114 and CP-225,917. Collection of Czechoslovak Chemical Communications, 65 (4). pp. 490-510. ISSN 0010-0765

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