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Tetrahedron Letters

Volumn 19, Issue 46, 1978, Pages 4543-4546

Petasinine and petasinoside, two minor alkaloids possessing a new necine isolated from petasites japonicus maxim.

(5) Yamada, Kiyoyuki a Tatematsu, Hiroshi a Unno, Ryoichi a Hirata, Yoshimasa a Hirono, Iwao b

a NAGOYA UNIVERSITY (Japan)

b UNIVERSITY OF TOKYO (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0004901393 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(01)95273-6 Document Type: Article

Times cited : (26)

References (20)

1
- 0015714462
- (1973) Gann , vol.64 , pp. 527
- Hirono¹ Shimizu² Fushimi³ Mori⁴ Kato⁵

2
- 0007705355
- ISOLATION AND THE STRUCTURES OF TWO NEW ALKALOIDS, PETASITENINE AND NEOPETASITENINE FROM PETASITES JAPONICUS MAXIM.
- (1976) Chemistry Letters , pp. 461
- Yamada¹ Tatematsu² Suzuki³ Hirata⁴ Haga⁵ Hirono⁶

3
- 0007657560
- STEREOCHEMISTRY OF PETASITENINE, THE CARCINOGENIC ALKALOID FROM PETASITES JAPONICUS MAXIM. AND TRANSFORMATION OF PETASITENINE TO SENKIRKINE
- (1976) Chemistry Letters , pp. 1123
- Yamada¹ Tatematsu² Hirata³ Haga⁴ Hirono⁵

4
- 0017063807
- (1976) Chem. Pharm. Bull. , vol.24 , pp. 1120
- Furuya¹ Hikichi² Iitaka³

5
- 0017329330
- (1977) J. Natl. Cancer Inst. , vol.58 , pp. 1155
- Hirono¹ Mori² Yamada³ Hirata⁴ Haga⁵ Tatematsu⁶ Kanie⁷

6
- 84914389053
- Satisfactory microanalyses or high resolution mass spectral data were obtained.

7
- 84914389052
- +), 259, 222, 122, 121, 120, 83.

8
- 84914389051
- The molecular formula of petasinoside (3) was determined by consideration of the physical and spectral properties of petasinoside triacetate (4). No molecular ion peak was observed In the mass spectrum of 3.

9
- 84914389050
- This doublet could not clearly be observed because of overlapping with other singnals arising from impurities.

10
- 84914389049
- +), 222, 182, 122, 121, 120, 108, 83.

11
- 84914389048
- +), 182, 122, 121, 120, 108, 83.

12
- 0001633498
- (1969) J. Org. Chem. , vol.34 , pp. 4137
- Aasen¹ Culvenor² Smith³

13
- 0006684892
- (1969) J. Org. Chem. , vol.34 , pp. 4143
- Aasen¹ Culvenor²

14
- 0008169666
- (1961) J. Am. Chem. Soc. , vol.83 , pp. 3323
- Adams¹ Miyano² Nair³

15
- 84914389047
- +), 293, 275, 220, 208, 179, 178.

16
- 84914389046
- +), 418, 352, 324, 273.

17
- 4244144203
- A study of 13CH coupling constants in hexopyranoses
- (1974) Journal of the Chemical Society, Perkin Transactions 2 , pp. 293
- Bock¹ Pedersen²

18
- 84914389045
- 13CH(1) coupling constant is increased by ca. 5 Hz In both anomers relative to that of the methyl glycosides.

19
- 84914389044
- The structure assignment for this compound was based on IR, NMR, and mass spectral evidence.

20
- 84914389043
- There Is a possibility that the migration of the angeloyl group in petasinine (1) occurred from C-2 to C-9 and subsequently the secondary hydroxyl group at C-2 was esterified with the acid chloride of 9, resulting in the formation of petasinoside triacetate (4). This possibility was excluded by the fact that no such acyl migration took place under the reaction conditions of converting 1 to 4.

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