Enantioselective total syntheses of allopumiliotoxins 267A, 323B', and 339A. Application of iodide-promoted iminium ion-alkyne cyclizations for forming allopumiliotoxin A alkaloids

Journal of the American Chemical Society

Volumn 118, Issue 38, 1996, Pages 9073-9082

  Caderas, Ristian ^a,b,c   Lett, Renee ^a,d   Overman, Larry E ^a   Rabinowitz, Michael H ^a,e   Robinson, Leslie A ^a,f   Sharp, Matthew J ^a,e   Zablocki, Jeffery ^a,g  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Schweizerische Nationalfonds SNF   (Switzerland)

^c Sandoz Pharma Ltd   (Switzerland)

^d DUPONT COMPANY   (United States)

^e GLAXOSMITHKLINE   (United States)

^f NOVARTIS PHARMA AG   (Switzerland)

^g AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 10244222753     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961640y     Document Type: Article

References (44)

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10. See the preceding paper in this issue for a full account of these investigations.
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39. Although either n- or s-BuLi can be employed, s-BuLi is preferable since a smaller excess is required to obtain optimum yields.
40. The contaminating amount of the C(11) epimer could not be removed until the alkylideneindolizidine ring was formed.
41. 3 for >5 min at -78 °C produced the internal alkene a as the major product. uation Presented
42. The overall yield was 21% when corrected for the isomeric purity of 39.
43. Bessard, Y.; Daly, J.; Overman, L. E.; Sharp, M. J.; Zablocki, J., manuscript in preparation.
44. For general experimental details, see: Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241.