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Stereospecific total synthesis of ajugarin-IV

✍ Scribed by Andrew S. Kende; Bruce Roth; Isao Kubo


Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
259 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis


A stereospecific sequence from the octalindlone 2 leads In 21 steps to the new lnsecttcrde ajuqarin-IV. Formation of the butenohde portion is conveniently achteved from acid 21 by successive use of the reaqents trts(tr~methylsiloxy)ethylene and ketenyhdenetrtphenyl-phosphorane.


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swrpnary Starting from alcohol 3, a stereospecific synthesis of carboxylic acid 1 is described. This acid 1 is a key lntermedlate in the total synthesis of aJugarins and its conversion into t 4-epi aJugarin is reported. A number of clerodane dlterpenes, as represented by aJugann 11a2, (I) and clerod

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