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

Authors
DOBLER M ANDERSON JC JUCH M BORSCHBERG HJ
Citation
M. Dobler et al., SYNTHESIS OF ARISTOTELIA-TYPE ALKALOIDS .15. TOTAL SYNTHESIS OF (-HOBARTINOL()), Helvetica Chimica Acta, 78(2), 1995, pp. 292-300
Citations number
22
Categorie Soggetti
Chemistry
Journal title
Helvetica Chimica Acta → ACNP
ISSN journal
0018019X
Volume
78
Issue
2
Year of publication
1995
Pages
292 - 300
Database
ISI
SICI code
0018-019X(1995)78:2<292:SOAA.T>2.0.ZU;2-9
Abstract
Synthetic (+)-makomakine (6) was transformed in six steps into (+)-(17 R,18R)-17,18-dihydrohobartine-17,18-diol ((+)-5) with an overall yield of 38% (Scheme 2). This compound was shown to be identical with natur al hobartinol, a monoterpene indole alkaloid from Aristotelia australa sica, originally believed to be the (17S)-epimer 1. At the same time, the synthesis of (+)-5 delineates the hitherto unknown absolute config uration of this metabolite.