Synthetic studies of microsclerodermins. A stereoselective synthesis of a core building block for (2S,3R,4S,5S,6S,11E)-3-Amino-6-methyl-12- (4-methoxyphenyl)-2,4,5-trihydroxydodec-11-enoic acid (AMMTD)

Tetrahedron Letters

Volumn 38, Issue 17, 1997, Pages 3013-3016

  Sasaki, Shigekazu ^a   Hamada, Yasumasa ^b   Shioiri, Takayuki ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; ANTIFUNGAL AGENT; CYCLOPEPTIDE;

ARTICLE; CHIRALITY; DRUG PURIFICATION; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030933126     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00522-4     Document Type: Article

References (16)

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2. Cf. Yokokawa, F.; Hamada, Y.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1996, 871.
3. Sharpless, K. B.; Amberg, W.; Bennan, Y. L.; Crispino, G. A.; Hartung, J.; Zhang, K. S. J. Org. Chem. 1992, 57, 2771.
4. Dondoni, A.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T. Synthesis 1994, 1450 and references therein.
5. For recent uses of aryl groups as the carboxyl synthon, see (a) Shioiri, T.; Hamada, Y.; Matsuura, F. Pure Appl. Chem. 1994, 66, 2151.
6. (b) Deng, J.; Hamada, Y.; Shioiri, T.; Matsunaga, S.; Fusetani, N. Angew. Chem. Int. Ed. Engl. 1994, 33, 1729.
7. (c) Shioiri, T.; Hamada, Y.; Matsuura, F. Tetrahedron, 1995, 51, 3939.
8. (d) Deng, J.; Hamada, Y.; Shioiri, T. J. Am. Chem. Soc. 1995, 117, 7824.
9. (e) Deng, J.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1996, 37, 2261.
10. Ley, S. V.; Anthony, N. J.; Armstrong, A.; Brasca, M. G.; Clarke, T.; Culshaw, D.; Greck, C.; Grice, P.; Jones, A. B.; Lygo, B.; Madin, A.; Sheppard, R. N.; Salawin, A. M. Z.; Williams, D. J. Tetrahedron Lett. 1989, 45, 7161.
11. Ceruti, M.; Balliano, G.; Viola, F.; Grosa, G.; Rocco, F.; Chattel, L. J. Med. Chem. 1992, 35, 2050.
12. The dihydroxylation using osmium tetroxide in the presence of N-methylmorpholine-N-oxide sluggishly proceeded to give a mixture of 13 and its diastereoisomer in a ratio of 1:1 after ketalization.
13. 3
14. Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2879.
15. 4, EtOH, 70-72% in 2 steps.
16. 7Si: C, 59.61; H, 9.80; N, 2.78. Found: C, 59.49; H, 9.56; N, 2.65.