Radical cyclization of β-alkoxyacrylates: Synthesis of a C2-symmetric, L-shaped molecule with four fused tetrahydropyran rings

Chirality

Volumn 12, Issue 5-6, 2000, Pages 360-361

  Lee, Eun ^a   Kim, Hee Jo ^a   Kang, Eun Joo ^a   Lee, In Su ^a   Chung, Young Keun ^a  

^a Seoul National University   (South Korea)

Author keywords

Four fused furon rings; L shaped molecule; Radical cyclization; alkoxyacrylate

Indexed keywords

ACRYLIC ACID; TETRAHYDROPYRAN DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CYCLIZATION; DERIVATIZATION; DRUG SYNTHESIS; ENZYME SUBSTRATE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0342657220     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(2000)12:5/6<360::AID-CHIR10>3.0.CO;2-1     Document Type: Article

References (12)

1. (a) Lee E, Tae JS, Lee C, Park CM. β-Alkoxyacrylates in radical cyclizations: remarkably efficient oxacycle synthesis. Tetrahedron Lett 1993;34:4831-4834.
2. (b) Lee E, Tae JS, Chong YH, Park YC, Yun M, Kim S. Fused oxacycle synthesis via radical cyclization of β-alkoxyacrylates. Tetrahedron Lett 1994;35:129-132.
3. (c) Lee E, Park CM. C-furanoside synthesis via radical cyclization of β-alkoxyacrylates. J Chem Soc Chem Comm 1994;:293-294.
4. (d) Lee E, Jeong J-w, Yu Y. Diastereoselective radical cyclization of chiral β-alkoxyacrylates. Tetrahedron Lett. 1997;38:7765-7768.
5. (e) Lee E, Park CM, Yun JS. Total synthesis of dactomelynes. J Am Chem Soc 1995;117:8017-8018.
6. (f) Lee E, Yoo S-K, Cho Y-S, Cheon H-S, Chong YH. Radical cyclization of β-alkoxyacrylates: stereoselective synthesis of (-)-trans-kumausyne. Tetrahedron Lett 1997;38:7757-7758.
7. (g) Lee E, Choi SJ. Radical cyclization of β-alkoxymethacrylates: expedient synthesis of (+)-methyl nonactate. Org Lett 1999;1:1127-1128.
8. Lee E, Yoo S-K, Choo H, Song HY. Radical cyclization of β-alkoxyacrylates: a formal synthesis of (-)-kumausallene. Tetrahedron Lett 1998; 39:317-318.
9. Lee E, Song HY, Kim HJ. Synthesis of (tetrahydrofuranyl)tetrahydrofurans via radical cyclization of bis (β-alkoxyacrylates). J Chem Soc Perkin I 1999;3395-3396.
10. For some of the more recent reiterative methods for preparation of fused tetrahydropyran systems, see: (a) Mori Y, Yaegashi K , Furukawa H. A new strategy for the reiterative synthesis of trans-fused tetrahydropyrans via alkylation of oxiranyl anion and 6-endo cyclization. J Am Chem Soc 1996;118:8153-8154.
11. 2-induced reductive intramolecular cyclization. Tetrahedron Lett 1999;40:2811-2814.
12. Sharpless KB, Amberg W, Bennani YL, Crispino GA, Hartung J, Jeong K-S, Kwong H-L, Morikawa K, Wang Z-M, Xu D, Zhang X-L. The osmium-catalyzed asymmetric dihydroxylation: a new ligand class and a process improvement. J Org Chem 1992;57:2768-2771.