Art

J-GLOBAL ID：200902248462208735   Reference number：09A0408022

NEW ENTRY TO THE ASYMMETRIC SYNTHESIS OF (-)-LASUBINE I AND (+)-SUBCOSINE I

(-)-ラスビンI及び(+)-スブコシンIの不斉合成への新しいエントリー

Author (5)： YAMAZAKI Naoki (Iwaki Meisei Univ., Fukushima, JPN) ,  YAMAZAKI Naoki (Tokyo univ. of Pharmacy and Life Sci., Tokyo, JPN) ,  ATOBE Masakazu (Tokyo univ. of Pharmacy and Life Sci., Tokyo, JPN) ,  KIBAYASHI Chihiro (Tokyo univ. of Pharmacy and Life Sci., Tokyo, JPN) ,  AOYAGI Sakae (Tokyo univ. of Pharmacy and Life Sci., Tokyo, JPN)
Material： Heterocycles  (International Journal for Reviews and Communications in Heterocyclic Chemistry)
Volume： 79  Page： 433-439  Publication year： Apr. 01, 2009 
JST Material Number： S0966A  ISSN： 0385-5414  CODEN： HTCYAM  Document type： Article
Article type： 短報  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： *alkaloid ,  *Lythraceae ,  ring-closing metathesis ,  lactonization ,  lactone ,  Michael reaction ,  annulation ,  *asymmetric synthesis ,  alicyclic compound ,  optical isomerism
Semi thesaurus term： Quinolizines

JST classification (2)： Other condensed derivatives of pyridine  (CF07097Y) ,  Alkaloids  (CF10030D)

Substance index (6)： (-)-Lasubine I ,  (+)-Subcosine I ,  (1R)-1-(2-Naphthyl)-2-[[(1S)-1-(3,4-dimethoxyphenyl)-3-butenyl]aminooxy]ethanol ,  Acrylic acid (1S,3S)-1-allyl-3-[(tert-butoxycarbonyl)amino]-3-(3,4-dimethoxyphenyl)propyl ester ,  [(1S)-1-(3,4-Dimethoxyphenyl)-2-[(2S)-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl]carbamic acid tert-butyl ester ,  (1S,5S,7S)-7-(3,4-Dimethoxyphenyl)-2-oxa-6-azabicyclo[3.3.1]nonane-3-one

Reference (14)：

• This paper is dedicated to the great contribution to heterocyclic chemistry by the late Dr. John Daly, National Institutes of Health.
• For isolation, see: K. Fuji, T. Yamada, E. Fujita, and H. Murata, Chem. Pharm. Bull., 1978, 26, 2515.
• For reviews of the lythraceae alkaloids, see:(a) W. M. Golebiewski and J. T. Wróbel,‘The Alkaloids,’ Vol.18, ed. by R. G. A. Rodrigo, Academic Press, New York, 1981, Chapter 4;(b) K. Fuji,‘The Alkaloids’, Vol.35, ed. by A. Brossi, Academic Press, San Diego, 1989, Chapter 3.
• For racemic syntheses of lasubine I, see:(a) H. Iida, M. Tanaka, and C. Kibayashi, J. Chem. Soc., Chem. Commun., 1983, 1143;(b) H. Iida, M. Tanaka, and C. Kibayashi, J. Org. Chem., 1984, 49, 1909;(c) H. Ent, H. De Koning, and W. N. Speckamp, Heterocycles, 1988, 27, 237;(d) A. L. J. Beckwith, S. P. Joseph, and R. T. A. Mayadunne, J. Org. Chem., 1993, 58, 4198;(e) V. Bardot, D. Gardette, Y. Gelas-Mialhe, J.-C. Gramain, and R. Remuson, Heterocycles, 1998, 48, 507;(f) B. Furman, and G. Lipner, Tetrahedron, 2008, 64, 3464. For asymmetric syntheses of (-)-lasubine I, see:(g) D. L. Comins and D. H. LaMunyon, J. Org. Chem., 1992, 57, 5807;(h) P. Chalard, R. Remuson, Y. Gelas-Mialhe, and J.-C. Gramain, Tetrahedron: Asymmetry, 1998, 9, 4361;(i) H. Ratoni and E. P. Kuendig, Org. Lett., 1999, 1, 1997;(j) F. A. Davis, A. Rao, and P. J. Carroll, Org. Lett., 2003, 5, 3855;(k) S. Liu, Y. Fan, X. Peng, W. Wang, W. Hua, H. Akber, and L. Liao, Tetrahedron Lett., 2006, 47, 7681.
• For racemic syntheses of lasubine II, see: refs. 4a, b and R. A. Pilli, L. C. Dias, and A. O. Maldaner, J. Org. Chem., 1995, 60, 717 and references cited therein. For asymmetric syntheses of (-)-lasubine II, see: ref. 4h and T. G. Back, M. D. Hamilton, V. J. J. Lim, and M. Parvez, J. Org. Chem., 2005, 70, 967 and references cited therein. For a synthesis of 8-epi-(-)-lasubine II, see: J. Lim and G. Kim, Tetrahedron Lett., 2008, 49, 88. For a synthesis of antipodal (+)-lasubines, see: O. G. Mancheño, R. G. Arrayás, J. Adrio, and J. C. Carretero, J. Org. Chem., 2007, 72, 10294 and references cited therein.

Terms in the title (3)： ラスビンI ,  不斉合成 ,  エントリー