1978
DOI: 10.1021/ja00481a033
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Synthesis of parazoanthoxanthins and pseudozoanthoxanthins

Abstract: Bell in ref 1, Chapter 1.(7) The variation in rate with P and r could come from variations in electron distribution, electron energies, rates of interspecies energy transfer, residence time in the plasma region, or simply from the rate law for the specific reactions. Changes in product composition (ratios) could also arise from all of these factors. In addition, the possibility of converting primary products to other materials has often been suggested and a major change in mechanism with conditions is not unli… Show more

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Cited by 40 publications
(17 citation statements)
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“…In extensions of Büchi’s seminal work, Horne reported marked improvements for the oxidative cyclizations to the phakellins and also the rearrangement of dibromophakellin ( 20 ) to dibromoisophakellin ( 22 ) at 130 °C involving a net N→C migration presumably involving an iminium intermediate 24 . 22 This process is conceptually similar to that described by Buchi for the synthesis of parazoanthoxanthin 23 and later revisited and elegantly expanded by Horne. 6c Feldman utilized sulfur oxidation by way of a Pummerer reaction to access the core structures of dibromophakellstatin and dibromoagelaspongin and proposed a key spiro intermediate 24 that overlaps with biomechanistic speculations.…”
Section: Structural Diversity Proposed Biosynthetic Hypotheses Anmentioning
confidence: 65%
“…In extensions of Büchi’s seminal work, Horne reported marked improvements for the oxidative cyclizations to the phakellins and also the rearrangement of dibromophakellin ( 20 ) to dibromoisophakellin ( 22 ) at 130 °C involving a net N→C migration presumably involving an iminium intermediate 24 . 22 This process is conceptually similar to that described by Buchi for the synthesis of parazoanthoxanthin 23 and later revisited and elegantly expanded by Horne. 6c Feldman utilized sulfur oxidation by way of a Pummerer reaction to access the core structures of dibromophakellstatin and dibromoagelaspongin and proposed a key spiro intermediate 24 that overlaps with biomechanistic speculations.…”
Section: Structural Diversity Proposed Biosynthetic Hypotheses Anmentioning
confidence: 65%
“…Dried parazoanthoxanthin A was dissolved either in triply distilled water or in the required buffer solution. The concentration of parazoanthoxanthin A was determined spectrophotometrically by using a molar extinction coefficient of ⑀ 295 (25°C) ϭ 37,500 M Ϫ1 cm Ϫ1 (15).…”
Section: Methodsmentioning
confidence: 99%
“…Intramolecular ring opening of N- (1,2,4-oxadiazol-3-yl)-b-enamino ketones 9 yields 4-acyl-2-aminoimidazoles only as minor products if they are 5-unsubstituted. 10 Conversion of 4-acyl-2-aminooxazoles into 4-acyl-2-aminoimidazoles occurs on treatment with ammonia or primary or secondary amines in 30-60% yields and with the formation of side products. 11 Regarding the synthesis of oroidin or keramadine derivatives, the amino group should be introduced after the Sonogashira coupling…”
Section: Figure 1 Target Structures and Retrosynthetic Cutsmentioning
confidence: 99%