Absolute configuration of methyl (2Z,6R,8R,9E)-3,6-epoxy-4,6,8-triethyl-2,4,9-dodecatrienoate from the sponge Plakortis halichondrioides

Tetrahedron Letters

Volumn 37, Issue 37, 1996, Pages 6681-6684

  Schmidt, Eric W ^a   Faulkner, D John ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,6 EPOXY 4,6,8 TRIETHYL 2,4,9 DODECATRIENOIC ACID METHYL ESTER; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG ISOLATION; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; SPONGE;

PLAKORTIS HALICHONDRIOIDES;

EID: 0030577018     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)01474-8     Document Type: Article

References (14)

1. 1. Higgs, M.D.; Faulkner, D.J. J. Org. Chem. 1978, 43, 3454.
2. 2. Faulkner, D.J. Nat. Prod. Rep. 1984, 1, 513 and subsequent reports in this series.
3. 3. a) De Guzman, F.S.; Schmitz, F.J. J. Nat. Prod. 1990, 53, 926.
4. b) Patil, A.D.; Freyer, A.J.; Carte, B.; Johnson, R.K.; Lahouratate, P. J. Nat. Prod. 1996, 59, 219. Relative stereochemistry was determined by NOE experiments.
5. 4. a) Kobayashi, M.; Kondo, K.; Kitagawa, I. Chem. Pharm. Bull. 1993, 41, 1324. This work, using Mosher's method, represents the first assignment of absolute configuration in this class of compounds.
6. b) Varoglu, M.; Peters, B.M.; Crews, P. J. Nat. Prod. 1995, 58, 27.
7. 5. We thank Dr. Ying-cai Peng of Zhongshan University, People's Republic of China, for bringing this problem to our attention and for proposing the revision of the double bond geometry at C-2.
8. D = -175°) was incorrectly reported.
9. 7. The sample had become a very pale yellow during storage.
10. 13C data were used to further substantiate several structures.
11. 9. Nagai, Y.; Kusumi, T. Tetrahedron Lett. 1995, 36, 1853.
12. 10. Soai, K.; Okawa, A.J. J. Org. Chem. 1986, 51, 4000.
13. 13C spectral data also confirmed the stereochemical assignments.
14. 12. We thank Dr. Jay S. Siegel (University of California, San Diego) for helpful comments on this manuscript. The ester 2 was originally isolated in our laboratory by Donald B. Stierle. This work was supported by the California Sea Grant College Program (NOAA grant NA36RG0537, project R/MP-60).