Base-catalyzed epimerization of the butenolide in annonaceous acetogenins

Chirality

Volumn 12, Issue 3, 2000, Pages 127-129

  Yu, Qian ^a   Wu, Yikang ^a   Wu, Yu Lin ^a   Xia, Li Jun ^a   Tang, Min Hua ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Chiral column; Chirality; DBU; Racemization; Separation

Indexed keywords

ACETOGENIN; BUTENOLIDE; NATURAL PRODUCT;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; RACEMIC MIXTURE;

4-BUTYROLACTONE; CATALYSIS; CIRCULAR DICHROISM; FURANS; LACTONES; STEREOISOMERISM;

EID: 0034090697     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(2000)12:3<127::AID-CHIR4>3.0.CO;2-E     Document Type: Article

References (19)

1. Rupprecht JK, Hui YH, McLaughlin JL. Annonaceous acetogenins: a review. J Nat Prod 1990;53:237-278.
2. Fang XP, Rieser, MJ, Gu ZM, McLaughlin JL. Annonaceous acetogenins: an updated review. Phytochem Anal 1993;4:27-48.
3. Zeng L, Ye Q, Oberlies NH, Shi GE, Gu ZM, He K, McLaughlin JL. Recent advances in Annonaceous acetogenins. Nat Prod Rep 1996; 275-306.
4. Cavé A, Figadère B, Laurens A, Cortes D. Acetogenins from Annonaceae. Prog Chem Org Nat Prod 1997;70:81-288.
5. Alali FQ, Liu X-X, McLaughlin JL. Annonaceous acetogenins: recent progress. J Nat Prod 1999;62:504-540.
6. Hoppe R, Scharf H-D. Annonaceous acetogenins - synthetic approaches towards a novel class of natural-products. Synthesis 1995;1447-1464.
7. Figadère B. Syntheses of acetogenins of Annonaceae - a new class of bioactive polyketides. Acc Chem Res 1995;28:359-365.
8. Casiraghi G, Zanardi F, Bottistini L, Rass G, Appendino G. Current advances in the chemical synthesis of Annonaceous acetogenins and relatives. Chemtracts 1998;11:803-827.
9. Yao Z-J, Wu Y-L. Total synthesis of (10ζ,15R,16S,20S,34R)-corossoline. Tetrahedron Lett 1994;35:157-160.
10. Yao Z-J, Wu Y-L. Synthetic studies toward mono-THF Annonaceous acetogenins: a diastereoselective and convergent approach to corossolone and (10RS)-corossoline. J Org Chem 1995;60:1170-1176.
11. Natito H, Kawahara E, Manita K, Maeda M, Sasaki S. The first total synthesis of (+)-bullatacin, a potent anititumor Annonaceous acetogenin, and (+)-(15,24)-bisepi-bullatacin. J Org Chem 1995;60:4419-4427.
12. Marshall JA, Jiang H-J. Total synthesis of the cytotoxic threo, trans, erythro, cis, threo Annonaceous acetogenin trilobin. J Org Chem 1999;64:971-975.
13. Hanessian S, Grillo TA. Stereocontrolled total synthesis of an Annonacin A-type acetogenin: pseudoannonacin A? J Org Chem 1998;63:1049-1075.
14. Yu Q, Wu Y-K, Ding H, Wu Y-L. The first total synthesis of 4-deoxy-annomontacin. J Chem Soc Perkin Trans 1 1999;1183-1188.
15. Evans PA, Murthy VS. Enantioselective synthesis of the 4-hydroxy butenolide terminus of mucocin and related Annonaceous acetogenins. Tetrahedron Lett 1998;39:9627-9628.
16. Takahashi S, Nakata T. Total synthesis of an anticancer agent, mucocin. 2. A novel approach to a γ-hydroxy butenolide derivative and completion of total synthesis. Tetrahedron Lett 1999;40:727-430.
17. Yu Q, Yao Z-J, Chen X-G, Wu Y-L. Total synthesis of (10R)- and (10S)-corossolin: determination of the stereochemistry at C-10 of the natural corossolin and the differential toxicity toward cancer cells caused by the configuration at C-10. J Org Chem 1999;64:2400-2445.
18. Duret P, Waechter A-I, Hocquemiller B, Cavé A, Piérard C, Pérès M. Assignment of absolute-configuration of the α,β-unsaturated γ-methyl-γ-lactone of the Annonaceous acetogenins by a simple enzymatic method. Tetrahedron Lett 1996;37:7043-7046.
19. Duret P, Figadère B, Hocquemiller R, Cavé A. Epimerization of Annonaceous acetogenins under basic conditions. Tetrahedron Lett 1997; 38:8849-8852.