An asymmetric synthesis of the BC ring system of 8-epitaxoids by way of intramolecular aldol and successive stereoselective methylation reactions

Chemistry Letters

Volumn , Issue 6, 1996, Pages 483-484

  Mukaiyama, Teruaki ^a   Shiina, Isamu ^a   Iwadare, Hayato ^a   Saitoh, Masahiro ^a   Nishimura, Koji ^a   Nishimura, Toshihiro ^a   Ohkawa, Naoto ^a   Sakoh, Hiroki ^a   Saitoh, Katsuyuki ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030489318     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.483     Document Type: Article

References (19)

1. Though this is not a formal nomenclature, the numbering of taxane system is used in this letter to correspond to other references. We thank Prof. N. Inamoto for his kind advice.
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4. Synthesis of AB ring model system; T. Mukaiyama, I. Shiina, K. Kimura, Y. Akiyama, and H. Iwadare, Chem. Lett., 1995, 229.
5. Synthesis of optically active AB ring system; I. Shiina, H. Iwadare, M. Saitoh, N. Ohkawa, T. Nishimura, and T. Mukaiyama, Chem. Lett., 1995, 781.
6. Retrosynthetic and synthetic studies; I. Shiina, M. Saitoh, K. Nishimura, K. Saitoh, and T. Mukaiyama., Chem. Lett., 1996, 223.
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9. Prof. G. Stork presented AB to ABC ring constructing strategy by intramolecular aldol reaction in Goto memorial lecture at Nagoya University on April 28th in 1995.
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17. 27 +13.4° (c 1.26, benzene).
18. 23 +80.3° (c 1.50, benzene).
19. The facile retro-aldol - aldol two step sequential reactions of taxol and its derivatives were already documented; D. G. I. Kingston, A. A. Molinero, and J. M. Rimoldi, Prog. Chem. Org. Nat. Prod., 61, 1 (1993).