Studies toward the tricyclic core of phomactin A. Synthesis of the reduced furanochroman subunit

Organic Letters

Volumn 2, Issue 16, 2000, Pages 2507-2509

  Seth, Punit P ^a   Totah, Nancy I ^a  

^a E11 SSH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOPYRAN DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FURAN DERIVATIVE; FUSED HETEROCYCLIC RINGS; PHOMACTIN A;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; SYNTHESIS;

BENZOPYRANS; FURANS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION;

EID: 0034632350     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0061788     Document Type: Article

References (15)

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2. (a) Chu, M.; Patel, M. G.; Gullo, V. P.; Truumees, I.; Puar, M. S. J. Org. Chem. 1992, 57, 5817.
3. (b) Chu, M.; Truumees, I.; Gunnarsson, I.; Bishop, W. R.; Kreutner, W.; Horan, A. C.; Gullo, V. P.; Puar, M. S. J. Antibiot. 1993, 46, 554.
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7. For previous work toward the synthesis of the tricyclic core of phomactin A, see: Foote, K. M.; Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 275.
8. Despite the observance of the 1-oxadecalin as the central component in a variety of natural products, direct elaboration of this system is rarely observed. Rather, manipulation of the carbon framework is followed by generation of a dihydropyran at a late stage of the synthesis. See, for example: Columbo, M. I.; Zinczuk, J.; Ruveda, E. A. Tetrahedron 1992, 48, 963.
9. Seth, P. P.; Chen, D.; Wang, J.; Gao, X.; Totah, N. I. Tetrahedron, in press.
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12. The stereochemistry of the major diastereomer was confirmed by NOE studies on a more advanced intermediate (cf. Figure 2).
13. Upon deprotonation (e.g., 16), β-elimination is presumably suppressed due to the orthogonal orientation of the β-alkoxy substituent relative to the enolate π system. See, for example: (a) Naef, N.; Seeback, D. Angew. Chem., Int. Ed. Engl. 1981, 20, 1030.
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