Total synthesis of (-)-mniopetal E, a novel biologically intriguing drimane sesquiterpenoid

Tetrahedron Letters

Volumn 40, Issue 44, 1999, Pages 7835-7838

  Suzuki, Yoshikazu ^a   Nishimaki, Ryoko ^a   Ishikawa, Makoto ^a   Murata, Takeshi ^a   Takao, Ken ichi ^a   Tadano, Kin ichi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

Biologically active compounds; Diels Alder reactions; Terpenoids

Indexed keywords

DRIMANE SESQUITERPENOID DERIVATIVE; MNIOPETAL E; NAPHTHALENE DERIVATIVE; SESQUITERPENOID; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOMER; PARTIAL DRUG SYNTHESIS; STEREOCHEMISTRY;

BETULACEAE;

EID: 0033615781     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01631-7     Document Type: Article

References (10)

1. 1. Kuschel, A.; Anke, T.; Velten, R.; Klostermeyer, D.; Steglich, W.; König, B. J. Antibiot. 1994, 47, 733.
2. 2. Velten, R.; Klostermeyer, D.; Steffan, B.; Steglich, W.; Kuschel, A.; Anke, T. J. Antibiot. 1994, 47, 1017.
3. 3. Ayer, W. A.; Craw, P. A. Can. J. Chem. 1989, 67, 1371.
4. 4. Velten, R.; Steglich, W.; Anke, T. Tetrahedron: Asymmetry 1994, 5, 1229.
5. 5. Murata, T.; Ishikawa, M.; Nishimaki, R.; Tadano, K. Synlett 1997, 1291.
6. 6. A recent report on natural product synthesis based on the IMDA approach, see: Ishihara, J.; Yamamoto, Y.; Kanoh, N.; Murai, A. Tetrahedron Lett. 1999, 40, 4387.
7. 7. For instance, we met difficulty in the oxidation of the hydroxylmethyl group, obtained by removal of the O-SEM group in 10, for generation of an aldehyde group.
8. 3) NMR, IR], and gave satisfactory HRMS except unstable intermediates. Yields refer to homogeneous samples purified by chromatography on silica gel.
9. 9. Fujita, E.; Nagao, Y; Kaneko, K. Chem. Pharm. Bull. 1978, 26, 3743.
10. +), m/z 296.1260, found 296.1263.