Preparation of helioporin D from the seco-pseudopterosin aglycone: Revision of the stereostructure of helioporin D

Tetrahedron Letters

Volumn 39, Issue 12, 1998, Pages 1541-1544

  Geller, Thomas ^a   Jakupovic, Jasmin ^a   Schmalz, Hans Günther ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; HELIOPORIN D; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032546284     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00020-3     Document Type: Article

References (13)

1. 1. Tanaka, J.-i.; Ogawa, N.; Liang, J.; Higa, T.; Gravalos, D.G. Tetrahedron 1993, 49, 811.
2. 2. Look, S.A.; Fenical, W. Tetrahedron 1987,43, 3363.
3. 3. a) Look, S.A.; Fenical, W.; Jacobs, R.S.; Clardy, J. Proc. Natl. Acad. Sci. USA 1986, 83, 6238;
4. b) Look, S.A.; Fenical, W.; Matsumoto; Clardy, J. J. Org. Chem. 1986, 51, 5140;
5. c) Roussis, V.; Wu, Z.; Fenical, W.; Strobel, S.A.; Van Duyne, G.; Clardy, J. J. Org. Chem. 1990, 55, 4916.
6. 4. Geller, T.; Schmalz, H.-G.; Bats, J.W. Tetrahedron Lett. 1998, 39, 1537.
7. 1H NMR of the helioporins B-F.
8. 6. We have independantly prepared analogeous compounds with an epimeric configuration at the sidechain chirality center (D. Hörstermann, H.-G. Schmalz, unpublished results).
9. 7. Majdalani, A.; Schmalz, H.-G. Synlett, 1997, 1303.
10. 8. Clark, J.H.; Holland, H.L., Miller, J.M. Tetrahedron Lett. 1976, 3361.
11. 9. The given coupling constants for 6 and 9 have been rounded to a multiple of 0.5.
12. 3).
13. 3 skeleton (B). (equation presented)