Isolation and Partial synthesis of 3(R)- and 3(S)-deoxypumiloside; structural revision of the key metabolite from the camptothecin producing plant, Ophiorrhiza pumila

Tetrahedron Letters

Volumn 38, Issue 24, 1997, Pages 4255-4258

  Kitajima, Mariko ^a   Masumoto, Seiji ^a   Takayama, Hiromitsu ^a   Aimi, Norio ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE ALKALOID;

ARTICLE; CIRCULAR DICHROISM; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYTOCHEMISTRY; PLANT; STEREOCHEMISTRY;

EID: 0030906773     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00858-7     Document Type: Article

References (13)

1. Wang, J. C. Ann. Rev. Biochem., 1985, 54, 665-697.
2. Priel, E.; Blair, D. G.; Showalter, S. D. U. S. PAT. APPL., 31 pp. avail. NTIS, order No. PAT-APPL-7-520 456.
3. Hutchinson, C. R. Tetrahedron, 1981, 37, 1047-1065.
4. Cai, J.-C.; Hutchinson, C. R. in The Alkaloids, Brossi, A., ed., Academic Press Inc., New York, 1983, Vol 21, pp. 101-137.
5. Wall, M. E.; Wani, M. C. in The Monoterpenoid Indole Alkaloids, Capter 13, (Saxton, J. E., ed.), John Wiley & Sons Ltd., London. 1994, pp. 689-713.
6. Aimi, N.; Nishimura, M.; Miwa, A.; Hoshino, H.; Sakai, S.; Haginiwa, J. Tetrahedron Lett., 1989, 30, 4991-4994.
7. Aimi, N.; Hoshino, H.; Nishimura, M.; Sakai, S.; Haginiwa, J. Tetrahedron Lett. 1990, 31, 5169-5172.
8. Aimi, N.; Ueno, M.; Hoshino, H.; Sakai, S. Tetrahedron Lett., 1992, 33, 5403-5404.
9. Carte, B. K.; DeBrosse, C.; Eggleston, D.; Hemling M.; Mentzer, M.; Poehland, B.; Troupe, N.; Westley, J. W.; Hecht, S. M. Tetrahedron, 1990, 46, 2747-2760
10. 3) δ: 161.8 (C-2), 61.5 (C-3), 48.5 (C-5), 128.0 (C-6), 130.0 (C-7). 127.7 (C-8), 127.9 (C-9), 126.7 (C-10), 129.5 (C-11), 129.0 (C-12), 148.2 (C-13), 30.0 (C-14), 28.3 (C-15), 108.4 (C-16), 146.8 (C-17), 120.8 (C-18), 131.5 (C-19), 42.9 (C-20), 96.4 (C-21), 162.8 (C-22), 96.1 (C-1′), 70.6 (C-2′), 72.4 (C-3′), 68.2 (C-4′), 72.3 (C-5′), 61.8 (C-6′), 20.74 and 20.65 (each CO-Me), 20.57 (2 × CO-Me), 170.6 and 170.1 (each CO-Me), 169.4 (2 × CO-Me); CD (c = 0.21 mmol/1, MeOH, 21°C) Δε (λ nm): 0 (330), +1.46 (320), +0.29 (317), +0.88 (313), +0.29 (310), +1.17 (307), +0.58 (303), +6.56 (276), 0 (266), -16.62 (247), -27.12 (238), 0 (225), -2.33 (218), 0 (213), +5.83 (208).
11. 3) δ: 161.9 (C-2), 60.2 (C-3), 47.9 (C-5), 128.0 (C-6), 130.4 (C-7), 127.6 (C-8), 127.9 (C-9), 126.7 (C-10), 129.5 (C-11), 129.1 (C-12), 148.2 (C-13), 28.8 (C-14), 23.8 (C-15), 110.4 (C-16), 145.1 (C-17), 121.6 (C-18), 131.4 (C-19), 43.8 (C-20), 96.3 (C-21), 165.2 (C-22), 96.1 (C-1′), 70.4 (C-2′), 72.4 (C-3′), 68.1 (C-4′), 72.2 (C-5′), 61.7 (C-6′), 20.8 and 20.7 (each CO-Me), 20.6 (2 × CO-Me), 170.6, 170.1, 169.9 and 169.4 (each CO-Me); CD (c = 0.15 mmol/1, MeOH, 21°C) Δε (λ nm): 0 (325), -1.01 (320), -0.40 (317), -0.81 (313), -0.40 (310), -0.60 (307), -0.20 (300), -25.15 (238), 0 (227), +3.62 (218), +10.87 (206).
12. Zheng, Q.; Yang, Y.; Martin, A. R. Heterocycles, 1994, 37, 1761-1772.
13. Cacchi, C.; Gattini, P. G.; Morea, E.; Orter G. Tetrahedron Lett., 1986, 27, 5541-5544.