Semipreparative synthesis, 13C- and 2D-NMR of Pulo'upone

Preparation of Bicyclo[4.3.0]nonanes by an Organocatalytic Intramolecular Diels–Alder Reaction

“…The research groups of Roush, [11] Nicolaou, [12] Boeckman, [13] Ley, [14] Kurth, [15] Jones, [16] Paquette, [17] Hase, [18] and Dias [19] have mostly used thermal IMDAs for the preparation of their target molecules. However, the triene precursor for the IMDA has to be chiral itself if a racemic mixture is to be avoided without use of a chiral catalyst.…”

“…Natural compounds related to amaminol A (1) and B (2), such as pulo'upones, [2] indanomycin (X-14547A), [3] 16deethylindanomycin (A83094A), [4] homoindanomycin, [5] cafamycin, [6] stawamycin, [7] cochleamycin A, [8] ikarugamycin, [9] and lepicidin A [10] have been synthesized by several different methods. The research groups of Roush, [11] Nicolaou, [12] Boeckman, [13] Ley, [14] Kurth, [15] Jones, [16] Paquette, [17] Hase, [18] and Dias [19] have mostly used thermal IMDAs for the preparation of their target molecules. However, the triene precursor for the IMDA has to be chiral itself if a racemic mixture is to be avoided without use of a chiral catalyst.…”

Adduct formed by chromium trioxide and zwitterionic quinolinic acid

“…The data have been deposited at the Cambridge Structural Database and the CCDC 720018 contains the supplementary crystallographic data for (quinolinium-3-carboxylato-O) trioxidochromium(VI). These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/ retrieving.html, or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; have utilized compound 2 in the synthesis of haminols [12], pulo'upone [13] and isopulo'upone [14]. The reaction mechanisms remain uncertain.…”

Synthesis of Ethyl 5Z,9Z,12Z‐octadecatrienoate (ethyl pinolenate) and Methyl 12Z,15Z‐octadecadienoate

“…We have for years successfully used the exceptionally simple and robust K 2 CO 3 mediated aqueous Wittig procedure [8] for the synthesis of various alkali isomerization products of pinolenic [2] and linolenic [4] acid esters, as well as other straight chain compounds [9,10] capable of producing hexahydroindenes via intramolecular DielsAlder reactions. We now report the results of using 2 as the ylide generating precursor in the potassium carbonate mediated one-pot aqueous double Wittig synthesis of methylene skipped cis diene and triene structures, and show that the obstacles just mentioned may be overcome to an extent.…”