SYNTHESIS OF VINCA ALKALOIDS AND RELATED-COMPOUNDS .73. SYNTHESIS ANDRING TRANSFORMATIONS OF DEETHYLASPIDOSPERMANE DERIVATIVES - SYNTHESISOF (-20-DEETHYL-3-OXOTABERSONINE())

Authors
KALAUS G JUHASZ I GREINER I KAJTARPEREDY M BRLIK J SZABO L SZANTAY C
Citation
G. Kalaus et al., SYNTHESIS OF VINCA ALKALOIDS AND RELATED-COMPOUNDS .73. SYNTHESIS ANDRING TRANSFORMATIONS OF DEETHYLASPIDOSPERMANE DERIVATIVES - SYNTHESISOF (-20-DEETHYL-3-OXOTABERSONINE()), Liebigs Annalen, (7), 1995, pp. 1245-1251
Citations number
16
Categorie Soggetti
Chemistry
Journal title
Liebigs Annalen → ACNP
ISSN journal
09473440
Issue
7
Year of publication
1995
Pages
1245 - 1251
Database
ISI
SICI code
0947-3440(1995):7<1245:SOVAAR>2.0.ZU;2-A
Abstract
The reaction of the key compound 14 with methyl 4-formyl-butanoate (9) or with 5-benzoyloxypentanal (13) gave the D-seco-aspidospermane deri vatives 17 and 18, respectively. Compound 17 was indirectly and 18 was directly converted to (+/-)-20-deethylvincadiffonnine (7) and (+/-)-2 0-deethyl-20-epivincadifformine (8). Epimerization occurred in both ca ses. The thioxo compound 23 was used for the synthesis of (+/-)-20-dee thyltabersonine (28) and (+/-)-20-deethyl-3-oxotabersonine (27). Oxida tive ring transformation of the (+/-)-20-deethylvincadifformine (7) ga ve (+/-)-16-deethylapovincamine (29).