Total synthesis of phomactin D

Tetrahedron Letters

Volumn 37, Issue 39, 1996, Pages 7107-7110

  Miyaoka, Hiroaki ^a   Saka, Yasuhiro ^a   Miura, Shotaro ^a   Yamada, Yasuji ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENOID; PHOMACTIN D; THROMBOCYTE ACTIVATING FACTOR ANTAGONIST; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030599229     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01585-7     Document Type: Article

References (19)

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6. 3. Synthetic study of phomactin A: Foote, K.M.; Hayes, C.J.; Pattenden, G. Tetrahedron Lett., 1996, 37, 275-278.
7. 4. a) Nagaoka, H.; Kobayashi, K.; Yamada, Y. Tetrahedron Lett., 1988, 29, 5945-5946;
8. b) Iwashima, M.; Nagaoka, H.; Kobayashi, K.; Yamada, Y. Tetrahedron Lett., 1992, 33, 81-82;
9. c) Nagaoka, H.; Shibuya, K.; Yamada, Y. Tetrahedron Lett., 1993, 34, 1501-1504.
10. 5. a) White, K.B.; Reusch, W. Tetrahedron, 1978, 34, 2439-2443;
11. b) Nagaoka, H.; Shibuya, K.; Kobayashi, K.; Miura, I.; Muramatsu, M.; Yamada, Y. Tetrahedron Lett., 1993, 34, 4039-4042 and references cited therein.
12. 6. Numbering of compounds is in accordance with that for phomactin D.
13. 7. Leonard, J.; Mohialdin, S.; Swain, P. A. Synth. Commun., 1989, 19, 3529-3534.
14. 8. The stereochemistry of 3 was determined by the NOESY spectrum of compound ii, which was converted from 3 via compound i, as shown below. Similar sequential Michael reaction has been reported by our laboratory. See: Nagaoka, H.; Kobayashi, K.; Okamura, T.; Yamada, Y. Tetrahedron Lett., 1987, 28, 6641-6644. (equation presented)
15. 1H-NMR analysis.
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17. 11. Alkenyliodide 16 was synthesized from 4-pentyn-1-ol in the following. cf: Negishi, E.; Van Horn, D.V.; King, A.O.; Okukado N. Synthesis, 1979, 501-502. (equation presented)
18. 2 was unsuccessful. cf: Takai, K.; Tagashira, M.; Kuroda, T.; Oshima, K.; Utimoto, K.; Nozaki, H. J. Am. Chem. Soc., 1986, 108, 6048-6050.
19. 13. Sharpless, K.B.; Michaelson, R.C. J. Am. Chem. Soc., 1973, 95, 6136-6137.