Construction of the diene moiety (C9-C18) of amphidinolide B, a 26- membered macrolide

Synlett

Volumn , Issue 5, 1999, Pages 571-572

  Ohi, Katsuhide ^a   Nishiyama, Shigeru ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

Amphidinolide B; Cytotoxic activity; Marine natural products

Indexed keywords

ALKADIENE; AMPHIDINOLIDE B; CARBON; MACROLIDE; NATURAL PRODUCT;

ARTICLE; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0032959858     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2690     Document Type: Article

References (17)

1. a) planar structure: Ishibashi, M.; Ohizumi, Y.; Hamashima, M.; Nakamura, H.; Hirata, Y.; Sasaki, T.; Kobayashi, J. Chem. Commun. 1987, 1127.
2. b) revised planar structure: Kobayashi, J.; Ishibashi, M.; Nakamura, H.; Ohizumi, Y.; Yamasu, T.; Hirata, Y.; Sasaki, T.; Ohta, T.; Nozoe, S. J. Nat. Prod. 1989, 52, 1036.
3. relative stereochemistry: Bauer, I.; Maranda, L.; Shimizu, Y.; Peterson, R. W.; Cornell, L.; Steiner, J. R.; Clardy, J. J. Am. Chem. Soc. 1994, 116, 2657.
4. absolute stereochemistry: Ishibashi, M; Ishiyama, H.; Kobayashi, J. Tetrahedron Lett. 1994, 35, 8241.
5. Ohi, K.; Shima, K.; Hamada, K.; Saito, Y.; Yamada, N.; Ohba, S.; Nishiyama, S. Bull. Chem. Soc. Jpn. 1998, 71, 2433.
6. Ohi, K.; Nishiyama, S. Synlett 1999, 573.
7. a) Chakraborty, T. K.; Suresh, V. R. Chem. Lett. 1997, 565.
8. b) Lee, D.-H.; Lee, S.-W. Tetrahedron Lett. 1997, 38, 7909.
9. Kobayashi, J.; Hatakeyama, A.; Tsuda, M. Tetrahedron 1998, 54, 697.
10. Cid, M. B.; Pattenden, G. Synlett 1998, 540.
11. a) Chakraborty, T. K.; Suresh, V. R. Tetrahedron Lett., 39 1998, 7775.
12. B) Chakraborty, T. K.; Suresh, V. R. Tetrahedron Lett. 1998, 39, 9109.
13. In the case of 2b, elevated reaction temperature (-40 °C → 0 °C) caused isomerization of the olefinic bond to give 4′. (figure presented)
14. This protective group was employed for compatibility with other functional groups in our synthetic process.
15. 2 (28%)].
16. 3I, nBuLi) of 9 afforded the olefinic isomer 10′ (20%), along with 10 (15%).
17. 3) δ 145.8, 139.3, 138.0, 128.2, 127.9, 127.7, 127.4, 113.4, 89.6, 80.7, 69.6, 63.1, 59.6, 42.3, 37.5, 32.5, 26.1, 24.5, 23.8, 18.5, 18.4, 14.2, and -5.1.