Synthetic study on hapalosin, a cyclic depsipeptide possessing multidrug resistance reversing activities

Tetrahedron Letters

Volumn 37, Issue 20, 1996, Pages 3467-3470

  Ohmori, Ken ^a   Okuno, Toshiaki ^a   Nishiyama, Shigeru ^a   Yamamura, Shosuke ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DEPSIPEPTIDE; HAPALOSIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; MULTIDRUG RESISTANCE; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0030009931     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00592-8     Document Type: Article

References (13)

1. Stratmann, K.; Burgoyne, D. L.; Moore, R. E.; Patterson, G. M. L. J. Org. Chem., 1994, 59, 7219-7226.
2. During preparation of this paper, two groups reported synthesis of 1. a) Dinh, T. Q.; Armstrong, R. W. J. Org. Chem. 1995, 60, 8118-8119. Ghosh, A. K.; Liu, W.; Xu, Y.; Chen, Z. Angew. Chem. Int. Ed. Engl. 1996, 35, 74-76.
3. During preparation of this paper, two groups reported synthesis of 1. a) Dinh, T. Q.; Armstrong, R. W. J. Org. Chem. 1995, 60, 8118-8119. Ghosh, A. K.; Liu, W.; Xu, Y.; Chen, Z. Angew. Chem. Int. Ed. Engl. 1996, 35, 74-76.
4. a) Maibaum, J.; Rich, D. H. J. Org. Chem. 1988, 53, 869-873.
5. b) Parkes, K. E. B.; Bushnell, D. J.; Crackett, P. H.; Dunsdon, S. J.; Freeman, A. C.; Gunn, M. P.; Hopkins, R. A.; Lambert, R. W.; Martin, J. A.; Merrett, J. H.; Redshaw, S.; Spurden, W. C.; Thomas, G. J. J. Org. Chem. 1994, 59, 3656-3664.
6. Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127-2129.
7. 3) δ 9.2, 14.1, 17.7, 18.5, 22.6, 25.5, 29.1, 29.3, 29.9, 31.0, 31.7, 37.5, 39.0, 41.2, 54.0, 70.6, 75.8, 81.8, 126.7, 128.6, 129.0, 136.9, 169.8, 173.4, 174.1.
8. Evans, D. A.; Ratz, A. M.; Huff, B. E.; Sheppard, G. S. Tetrahedron Lett. 1994, 35, 7171-7172.
9. 3) major confomer: δ 0.02 - 0.19 (6H, complex), 0.52 (3H, d, J= 6.8 Hz), 0.86 - 0.92 (6H, complex), 0.95 (9H, s), 1.17 (3H, d, J= 7.6 Hz), 1.20 - 1.49 (11H, complex), 1.95 - 2.05 (2H, complex), 2.30 (1H, dd, J= 10.0, 12.8 Hz), 2.54 (1H, dd, J= 5.6, 16.2 Hz), 2.76 (1H, dd, J= 2.4, 16.2 Hz), 2.87 (1H, m), 3.34 (1H, dd, J= 2.1, 12.8 Hz), 3.72 (1H, ddd, J= 2.1, 7.9, 10.0 Hz), 3.88 (1H, ddd, J= 2.4, 5.6, 7.9 Hz), 4.22 (1H, d, J= 8.8 Hz), 5.16 (1H, m), 7.08 - 7.31 (5H, complex).
10. Treatment with TBAF to remove a silyl protective group resulted in an inseparable mixture.
11. Shioiri, T.; Hayashi, K.; Hamada, Y. Tetrahedron 1993, 49, 1913 - 1924.
12. 3) major conformer: 12.1, 14.1, 17.5, 18.3, 22.6, 26.0, 28.0, 28.2, 28.8, 29.1, 29.2, 31.7, 36.4, 37.0, 40.7, 61.4, 70.2, 73.8, 76.5, 127.0, 128.9, 129.7, 137.4, 168.5, 168.7, 172.7.
13. The same observation was reported by Armstrong (see ref.2a).