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SYNTHESIS OF ARISTOTELIA-TYPE ALKALOIDS .15. TOTAL SYNTHESIS OF (+)-HOBARTINOL

DOBLER, M; ANDERSON, JC; JUCH, M; BORSCHBERG, HJ; (1995) SYNTHESIS OF ARISTOTELIA-TYPE ALKALOIDS .15. TOTAL SYNTHESIS OF (+)-HOBARTINOL. HELV CHIM ACTA , 78 (2) 292 - 300.

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Abstract

Synthetic (+)-makomakine (6) was transformed in six steps into (+)-(17R,18R)-17,18-dihydrohobartine-17,18-diol ((+)-5) with an overall yield of 38% (Scheme 2). This compound was shown to be identical with natural hobartinol, a monoterpene indole alkaloid from Aristotelia australasica, originally believed to be the (17S)-epimer 1. At the same time, the synthesis of (+)-5 delineates the hitherto unknown absolute configuration of this metabolite.

Type: Article
Title: SYNTHESIS OF ARISTOTELIA-TYPE ALKALOIDS .15. TOTAL SYNTHESIS OF (+)-HOBARTINOL
Keywords: PEDUNCULARINE
UCL classification: UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry
URI: http://discovery.ucl.ac.uk/id/eprint/80035
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