Formation of medium-ring diolides via intramolecular Diels-Alder reactions of dicarboxylic ester-tethered trienes

Tetrahedron Letters

Volumn 37, Issue 4, 1996, Pages 535-538

  Craig, Donald ^a   Ford, Mark J ^b   Stones, James A ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b AgrEvo UK Limited   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIKETONE; ETHER DERIVATIVE; MACROCYCLIC COMPOUND;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

BETULACEAE;

EID: 0030052773     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02181-7     Document Type: Article

References (17)

1. (i) Craig, D.; Reader, J. C. Tetrahedron Lett. 1990, 31, 6585;
2. (ii) Craig, D.; Reader, J. C. Tetrahedron Lett. 1992, 33, 4073;
3. (iii) Craig, D.; Reader, J. C. Tetrahedron Lett. 1992, 33, 6165;
4. (iv) Craig, D.; Reader, J. C. Synlett 1992, 757.
5. 2-symmetric tethers in type 2 IMDA processes, see: Shea, K. J.; Gauthier, R. J., Jr. Tetrahedron Lett. 1994, 35, 7311.
6. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: Oxford, 1983, chapter 3.
7. For an account of the use of the IMDA reaction for the synthesis of members of the cytochalasan family of macrolactones, see: Thomas, E. J. Acc. Chem. Res. 1991, 24, 229.
8. Aldrich Chemical Company.
9. 4 reduction of the corresponding acid.
10. 3N, DMSO) and olefination with methoxycarbonyl-methylenetriphenylphosphorane in situ (62% for the two-step, one-pot sequence) followed by desilylation (HCl, MeOH; 89%).
11. Yields cited herein are for pure materials, characterised by nmr, ir, low-resolution ms, and either high-resolution ms or elemental combustion analysis.
12. Compound 8: mp 123-124°C.
13. We thank Dr D. J. Williams and Mr A. J. P. White of this Department for the X-ray structure determinations described herein.
14. Compound 10: mp 127-128°C.
15. Compound 11: mp 154°C.
16. Corey, E. J.; Petrzilka, M. Tetrahedron Lett. 1975, 2537.
17. For example, we are looking at the synthesis and asymmetric IMDA reactions of trienes possessing bis(TBDPS)tartrate spacers as informational control elements.