Asymmetric synthesis of stellettamides A and C

Heterocycles

Volumn 75, Issue 2, 2008, Pages 285-290

  Yamazaki, Naoki ^a   Suzuki, Takeshi ^a   Yoshimura, Yuta ^a   Kibayashi, Chihiro ^a   Aoyagi, Sakae ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

Aminomethylindolizidine; Calmodulin Inhibitory Activity; Energy Dispersive X Ray Spectrum; Marine Sponge; Optical Rotation

Indexed keywords

EID: 43949089502     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-07-11211     Document Type: Article

References (14)

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8. Ishii K., Sone T., Shigeyama T., Noji M., and Sugiyama S. Tetrahedron 62 (2006) 10865
9. A solution of 11(98.0 mg, 0.753 mmol) and 9 (69.0 mg, 0.503 mmol) in benzene (5 mL) was heated to reflux using a Dean-Stark apparatus for water removal. After 24 h, the mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane-EtOAc, 2:1) to give 12 (99.5 mg, 91 %) as a colorless oil.
10. 4), and evaporated in vacuo. Purification of the residue by column chromatography (hexane-EtOAc,10:1) gave 14 (77.7 mg, 67%) as a colorless oil.
11. Corey E.J., and Ha D.-C. Tetrahedron Lett. 29 (1988) 3171
12. 3) δ1.07 (3H, d, J = 6.8 Hz), 1.35-1.53 (2H, m),1.58 (3H, s), 1.60 (3H, s), 1.68 (3H, d, J = 0.5 Hz), 1.93-2.03 (4H, m), 2.03-2.11(2H, m), 2.29-2.42 (1H, m), 5.04-5.13 (2H, m), 5.79 (1 H, dd, J =15.7, 0.8 Hz), 6.99 (1 H, dd, J =15.6, 7.9 Hz).
13. Hawarth R.D., Perkin Jr. W.H., and Pink H.S. J. Chem. Soc. (1926) 1709
14. The optical rotation was measured using a 100 mm length quartz cell with a methanolic solution, which was prepared 1 hour in advance by using a 2-mL volumetric flask.