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Tetrahedron Letters

Volumn 32, Issue 43, 1991, Pages 6129-6132

Preparation of spiroindolines as potential intermediates in aspidosperma alkaloid synthesis

(5) Troin, Yves a Sinibaldi, Marie Eve a Gramain, Jean Claude a Rubiralta, Mario b Diez, Anna b

a CNRS (France)

b UNIVERSITY OF BARCELONA (Spain)

Author keywords

enaminoesters; indoline; photocyclization; regioselective alkylation; tricyclic spiroindoline

Indexed keywords

ALKALOID; INDOLE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; PHOTOCHEMISTRY; PRIORITY JOURNAL; SYNTHESIS;

ASPIDOSPERMA;

EID: 0025939844 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/0040-4039(91)80770-7 Document Type: Article

Times cited : (10)

References (23)

1
- 0025123570
- and references cited therein.
- (1990) J. Org. Chem. , vol.55 , pp. 5483
- Dufour¹ Gramain² Husson³ Sinibaldi⁴ Troin⁵

2
- 0002508799
- (1985) Tetrahedron Lett. , vol.26 , pp. 2323
- Gramain¹ Husson² Troin³

3
- 84986468956
- A short and efficient synthesis of 4a-substitutedcis-hexahydro-1,2,3,4,4a,9a-carbazol-4-ones
- (1988) Journal of Heterocyclic Chemistry , vol.25 , pp. 201
- Gramain¹ Husson² Troin³

4
- 0025328387
- The synthesis of related tetracyclic spiroindolines lacking the acetate chain at the C-2 position has been recently reported:
- (1990) Tetrahedron Lett. , vol.31 , pp. 3779
- Rubiralta¹ Diez² Vila³

5
- 0024846433
- For intramolecular Mannich cyclization, see:, and references cited therein.
- (1989) J. Org. Chem. , vol.54 , pp. 5591
- Rubiralta¹ Ciez² Bosch³ Solans⁴

6
- 0001274215
- (1990) Tetrahedron , vol.46 , pp. 4049
- Mittendorf¹ Hiemstra² Speckamp³

7
- 84918692556
- 3 have a cis relationship.

8
- 0022541882
- (1986) J. Org. Chem. , vol.51 , pp. 1498
- Melillo¹ Cvetovich² Ryan³ Sletziwger⁴

9
- 84918657999
- All new compounds gave satisfactory spectral data and elemental analysis.

10
- 84918693204
- Formation of 6 can be attributed to the use of a secondry amine instead of a primary one, whose largerer steric hindrance promotes the reaction to occur preferentially upon the ester group.

11
- 84918676891
- max 289 nm.

12
- 2342653612
- (1984) J. Chem. Research. (M). , pp. 3401
- Nixon¹ Sheimann²

13
- 0002443990
- (1978) Org. Syn. , vol.57 , pp. 62
- Bryson¹ Dolak²

14
- 84918662122
- Similar isomerization was recently described: see ref. 6

15
- 0041753373
- For some photocyclizations with NH compounds see:, and references cited therein.
- (1980) Tetrahedron , vol.36 , pp. 1757
- Schultz¹ Sha²

16
- 84918704832
- 5), 124.5, C [[Truncated]]

17
- 84918669919
- 13C NMR spectrum.

18
- 84918694051
- 3)gd 26.8, 35.2, 51.2, 51.9, 52.9, 56.6, 68.2, 108.2, 117.2, 118.8, 123.9, 127.1, 127.5, 128.8, 130.2, 137.8, 150.9, 171.0, 171.3.

19
- 84918680734
- 3) δ 50.7, 50.9, 107.5, 110.3, 120.7, 122.0, 122.9, 127.1, 128.1, 128.9, 134.5, 135.9, 136.7, 165.4.

20
- 0011491177
- Structure determination of a tetrasaccharide: transient nuclear Overhauser effects in the rotating frame
- 3 was observed in a ROE spectrum at 300 MHz. For structure determination by ROE experiments: see
- (1984) Journal of the American Chemical Society , vol.106 , pp. 811
- Bother-By¹ Stephens² Lee³ Warren⁴ Jeanloz⁵

21
- 84918695114
- We thank Dr. G. Massiot and Dr. C. Lavaud for ROE experiments.

22
- 84984191293
- Amides from Nitriles using Basic Hydrogen Peroxide under Phase-Transfer Catalysed Conditions
- (1980) Synthesis , pp. 243
- Cacchi¹ Misiti² Latorre³

23
- 84918681783
- 3) δ 34.2, 46.3, 51.4, 52.0, 56.4, 69.1, 108.3, 119.1, 122.2, 127.1, 127.6, 128.9, 129.5, 130.0, 137.6, 151.1, 172.1, 175.3, 177.1.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.