First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin

Organic Letters

Volumn 6, Issue 4, 2004, Pages 553-556

  Suzuki, Takahiro ^a   Usui, Kenji ^a   Miyake, Yoshiharu ^a   Namikoshi, Michio ^b   Nakada, Masahisa ^a  

^a WASEDA UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF MARINE SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKENYL GROUP; ANTIMITOTIC AGENT; CARBOXYL GROUP; METHYL GROUP; PHOMOPSIDIN; PINENE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HORNER WADSWORTH EMMONS REACTION; STEREOCHEMISTRY; TEMPERATURE;

ANTINEOPLASTIC AGENTS; ASCOMYCOTA; CATALYSIS; CYCLIZATION; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PENTANOIC ACIDS; STEREOISOMERISM; TETRAHYDRONAPHTHALENES;

EID: 1342332912     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036338q     Document Type: Article

References (19)

1. Namikoshi, M.; Kobayashi, H.; Yoshimoto, T.; Hosoya, T. J. Antibiot. 1997, 50, 890-892.
2. Namikoshi, M.; Kobayashi, H.; Yoshimoto, T.; Meguro, S.; Akano, K. Chem. Pharm. Bull. 2000, 48, 1452-1457.
3. Kobayashi, H.; Meguro, S.; Yoshimoto, T.; Namikoshi, M. Tetrahedron 2003, 59, 455-459.
4. For reviews, see: Roush, W. R. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 513-550 and references therein and in ref 6.
5. Wakui, F.; Harimaya, K.; Iwata, M.; Sashita, R.; Chiba, N.; Mikawa, T. Jpn. Kokai Tokkyo Koho JP 07,126,211, May 16, 1995, Appl. Oct. 29, 1993; Chem. Abstr. 1995, 123, 105272b.
6. Wakui, F.; Harimaya, K.; Iwata, M.; Sashita, R.; Chiba, N.; Mikawa, T. Jpn. Kokai Tokkyo Koho JP 07,126,211, May 16, 1995, Appl. Oct. 29, 1993; Chem. Abstr. 1995, 123, 105272b.
7. Marsault, E.; Toró, A.; Nowak, P.; Deslongchamps, P. Tetrahedron 2001, 57, 4243-4260.
8. Piers, E.; Wong, T.; Coish, P. D.; Rogers, C. Can. J. Chem. 1994, 72, 1816-1819.
9. Midland, M. M.; McDowell, D. C.; Hatch, R. L.; Tramontano, A. J. Am. Chem. Soc. 1980, 102, 867-869.
10. Another diastereomer could not be observed by 400 MHz NMR.
11. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483 and references therein.
12. (b) Colberg, J. C.; Rane, A.; Vaquer, J.; Soderquist, J. A. J. Am. Chem. Soc. 1993, 775, 6065-6071.
13. Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U.-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461-5464. Other methods resulted in low yield because Weinreb amide 13 readily recyclized to afford lactone 3 as mentioned in the text.
14. Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 779, 6496-6511.
15. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769-3772.
16. Negishi, E. Pure Appl. Chem. 1981, 53, 2333-2356 and references therein.
17. Wipf, P.; Lim, S. Angew. Chem., Int. Ed. Engl. 1993, 32, 1068-1071.
18. For reviews, see: (a) Roush. W. R. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 435-480 and references therein, (b) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93 (6), 2117-2188.
19. For reviews, see: (a) Roush. W. R. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 435-480 and references therein, (b) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93 (6), 2117-2188.