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Total synthesis of methyl (±)-8α-carboxymethylpodocarpan-13-one-4β-carboxylate, a degradation product of steviol

✍ Scribed by Kenji Mori; Masanao Matsui

Publisher: Elsevier Science
Year: 1965
Tongue: French
Weight: 260 KB
Volume: 6
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)90188-6

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✦ Synopsis

Deceived 17 llay 1963) Steviol (Ia) ie the aglycone of mtevioside, a glycoeide almudaut in Stevia rebaudiena (1). Ita etructure, inoluding absolute stereoohemimtry, haa been dotermined by de&radative studies coupled with ODD measurementa

(2,3). Keoent disooverty of its gibberellin-like activity (4) prompted us to searoh a poaaible route to th.e total eynthesis of steviol, ae veil ae that of kaurenoic acid (Ia, C-13-H instead of -OH). In this oozemu& oation, a l tereo~elective total syntheeis of (k)-eeco aoid (II,)-vi11 be deroribed. The aeco acid (118) has been obtained an one of the oeonolyeis produots of ateviol methyl ester (Ib) and retains all the aaynmetric centers of steviol except one at C-13 (3).

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