Syntheses of (+/-)-17 alpha- and (+/-)-17 beta-hydroxytacamonine; Determination of configuration at C-17

被引：3

作者：

Belle, DD ^{[1
]}

Tolvanen, A ^{[1
]}

Lounasmaa, M ^{[1
]}

机构：

[1] TECH UNIV HELSINKI,ORGAN & BIOORGAN CHEM LAB,SF-02150 ESPOO,FINLAND

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 52期

关键词：

D O I：

10.1016/0040-4039(95)02047-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both (+/-)-17 alpha-hydroxytacamonine (3) and its 17 beta-isomer (4) were synthesized in two steps (one-pot) from aldehyde mixture 5/6 via the cyanohydrin reaction. NMR spectral characterization of isomer 3 revealed it to be unidentical with natural 17-hydroxytacamonine, whereas spectral data of isomer 4 were in agreement with those published for the natural isomer. The configuration at C-17 was confirmed by NOE difference spectroscopy.

引用

页码：9559 / 9560

页数：2

共 6 条

[1] PARTIAL SYNTHESIS OF (20S)-PSI-VINCAMINE AND (20S)-EPI-16 PSI-VINCAMINE [J].

LEMEN, J ;

CARONSIGAUT, C ;

HUGEL, G ;

LEMENOLIVER, L ;

LEVY, J .

HELVETICA CHIMICA ACTA, 1978, 61 (02) :566-570

[2] TOTAL SYNTHESIS OF THE INDOLE ALKALOID (+/-)-TACAMINE [J].

LOUNASMAA, M ;

BELLE, DD ;

TOLVANEN, A .

TETRAHEDRON LETTERS, 1994, 35 (33) :6151-6154

[3] TOTAL SYNTHESIS OF THE INDOLE ALKALOID (+/-)-TACAMONINE [J].

LOUNASMAA, M ;

BELLE, DD ;

TOLVANEN, A .

TETRAHEDRON LETTERS, 1995, 36 (39) :7141-7144

[4]

MASSIOT G, 1982, B SOC CHIM FR II-CH, P185

[5] ALDEHYDE INTERMEDIATES IN THE SYNTHESIS OF TACAMINE-TYPE INDOLE ALKALOIDS - PREPARATION OF (+/-)-APOTACAMINE [J].

TOLVANEN, A ;

BELLE, DD ;

LOUNASMAA, M .

HELVETICA CHIMICA ACTA, 1994, 77 (03) :709-715

[6] PHARMACOGNOSTICAL STUDIES OF TABERNAEMONTANA SPECIES .4. ALKALOIDS OF TABERNEMONTANA-EGLANDULOSA [J].

VANBEEK, TA ;

VERPOORTE, R ;

SVENDSEN, AB .

TETRAHEDRON, 1984, 40 (04) :737-748

← 1 →