Synthesis of Aristotelia-Type Alkaloids. Part XV. Total synthesis of (+)-hobartinol |
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Authors: | Markus Dobler,James C. Anderson,Mathias Juch,Hans-Jü rg Borschberg |
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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. |
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