Woodinine and its Stereomers - Absolute Configuration

✍ Scribed by Siavosh Mahboobi; Thomas Burgemeister; Wolfgang Wiegrebe

• Publisher: John Wiley and Sons
• Year: 1993
• Tongue: English
• Weight: 444 KB
• Volume: 326
• Category: Article
• ISSN: 0365-6233
• DOI: 10.1002/ardp.19933260108

✦ Synopsis

The synthesis of all the four stereomers of the alkaloid woodinine (12a)') is described and the stereochemical conclusions of Psi:?) and Still6) are discussed. The absol. configurations of woodinine (12a) and its diastereomer 8b are unequivocally deduced from the pertinent piperazinediones 16 and 17.

Woodinin und seine

Stereomeren -Absolute Konfiguration Die Synthese aller vier Stereomerer des Alkaloids Woodinin (12a)') wird beschrieben, die stereochemischen Ruckschlusse von Pai's') bzw. Stif/') werden diskutiert. Anhand der Piperazindione 16 and 17 wird die absol. Konfiguration von Woodinin (12a) und des Diastereomers 8b bewiesen. Recently we have described the synthesis of the alkaloid woodinine (12a, Scheme 2)'). The key step was the condensation of 5-bromotryptamine (1) with (S)-(-)-N-Boc-pyrrolidine-2-carboxaldehyde'). When we condensed 5-bromotryptamine (1) with R-(+)-N-Boc-pyrrolidine-2-carboxaldehyde (2) (Scheme I), prepared from D-proline as described for the S-enantiomer'), we 1) OHC-0-COCH, 2) CF&OOH, O", N2 (&) Br D T $ ; R 1 H N -~2 U 5: R' = CHO, R2 = BOC 6: R' = CHO, R2 =