2003
DOI: 10.1002/ejoc.200300057
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Enantioselective Synthesis of Clavepictine Analogues and Evaluation of Their Cytotoxic Activity

Abstract: Six analogues (labeled 27 to 32) of a cytotoxic alkaloid isolated from the tunicate Clavelina picta were synthesized from an acyl oxazolidine. The absolute stereochemistry of the targeted analogues derived from (R)-phenyl glycinol and the relative stereochemistries of three of the four stereocentres present in the molecule were set up by stereocontrolled additions to transient iminium ions. The main features of this synthesis include (i) a high level of stereocontrol for all the steps involving the arrangement… Show more

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Cited by 28 publications
(16 citation statements)
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“…533 An initial attempt at expanding the structure-activity relationship of the cytotoxic quinolizidine alkaloid clavepictine B isolated from the Bermudian ascidian Clavelina picta, 534 has indicated the importance of sidechain unsaturation, and that relative stereochemistry about the ring system does not seem to be important for cytotoxicity. 535 Two full accounts of the stereoselective synthesis of lepadiformine, a biologically active alkaloid isolated from the ascidians Clavelina lepadiformis and C. moluccensis, 536,537 have been reported. 538, 539 The structurally related ascidian alkaloids (+)-cylindricines C-E, isolated from an Australian collection of Clavelina cylindrica, 540 were prepared using ruthenium-catalysed hydrative diyne cyclisation methodology.…”
Section: Tunicates (Ascidians)mentioning
confidence: 99%
“…533 An initial attempt at expanding the structure-activity relationship of the cytotoxic quinolizidine alkaloid clavepictine B isolated from the Bermudian ascidian Clavelina picta, 534 has indicated the importance of sidechain unsaturation, and that relative stereochemistry about the ring system does not seem to be important for cytotoxicity. 535 Two full accounts of the stereoselective synthesis of lepadiformine, a biologically active alkaloid isolated from the ascidians Clavelina lepadiformis and C. moluccensis, 536,537 have been reported. 538, 539 The structurally related ascidian alkaloids (+)-cylindricines C-E, isolated from an Australian collection of Clavelina cylindrica, 540 were prepared using ruthenium-catalysed hydrative diyne cyclisation methodology.…”
Section: Tunicates (Ascidians)mentioning
confidence: 99%
“…Finally, stereoselective addition of vinylmagnesium bromide to a transient iminium ion generated from the amino ether moiety in 56 gave rise to the third stereocenter in 58, whereas reduction of 57 followed by N-and Odebenzylation gave 59 (Scheme 11). Scheme 11 The hydroxyoxazolidine 54 recently served as a starting material for the synthesis of more complex target compounds: [38] such as quinolizidine heterocycles 60. These molecules were designed with the aim of improving the cytotoxic activity of an alkaloid 61 named clavepictine A, isolated from a tunicate.…”
Section: Synthesis and Reactivity Of N-boc-2-acyloxazolidinesmentioning
confidence: 99%
“…The cytotoxic ascidian alkaloids clavepictine A 359 and clavepictine B 360 have served as models for the synthesis of a range of analogues for further biological evaluation. 167 In the key step, base-induced cyclisation of the chiral tetra-substituted piperidine 361 (LDA, THF, −78…”
Section: Alkaloids From Marine Sourcesmentioning
confidence: 99%