Enantioselective synthesis of reported hippospongic acid A

Synlett

Volumn , Issue 7, 1998, Pages 729-730

  Hioki, Hideaki ^a   Ooi, Hidenori ^a   Mimura, Yumi ^a   Yoshio, Suzuyo ^a   Kodama, Mitsuaki ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002451939     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1781     Document Type: Article

References (11)

1. Ohta, S.; Uno, M.; Tokumasu, M.; Hiraga, Y.; Ikegami, S. Tetrahedron Lett. 1996, 37, 7765.
2. Ohta, S.; Uno, M.; Yoshimura, M.; Hiraga, Y.; Ikegami, S. Tetrahedron Lett. 1996, 37, 2265.
3. For the synthesis of 2, see Takagi, R.; Sasaoka, A.; Kojima, S.; Ohkata, K. J. Chem. Soc., Chem. Commun. 1997, 1887;
4. Snider, B. B.; He, F. Tetrahedron Lett. 1997, 38, 5453.
5. Kodama, M.; Minami, H.; Mima, Y.; Fukuyama, Y. Tetrahedron Lett. 1990, 31, 4025;
6. Kodama, M.; Yoshio, S.; Yamaguchi, S.; Fukuyama, Y.; Takayanagi, H.; Morinaka, Y.; Usui, S.; Fukazawa, Y. Tetrahedron Lett. 1993, 34, 8453.
7. 5 The optical purity was >98% ee as analyzed by GC using chiral Column.
8. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakizawa, H. J. Am. Chem. Soc. 1991, 113, 4092;
9. Kusumi, T. J. Syn. Org. Chem. Jpn. 1993, 51, 462.
10. 3 in pyridine have been examined, but the yields of the desired exomethylene derivative were less than 35% because of the formation of an unstable product (probably a compound containing a tetrasubstituted double bond).
11. 3) 170.1 (C-1), 140.6 (C-2), 135.8, 135.0, 134.9 (C-5′, C-9′, C-13′), 132.6 (C-6), 131.2 (C-17′), 127.1 (C-8), 125.0 (C-1′), 124.4, 124.2, 124.2, 123.5 (C-4′, C-8′, C-12′, C-16′), 75.6 (C-3), 67.1 (C-7), 39.7 (C-6′, C-10′, C-14′), 33.7 (C-4), 32.9 (C-5), 28.2, 27.3 (C-2′, C-3′), 26.8, 26.7, 26.6 (C-7′, C-11′, C-15′), 25.7 (C-18′), 17.7 (C-22′), 16.1, 16.0, 16.0 (C-19′, C-20′, C-21′).