Simultaneous preparation of four truncated analogues of discodermolide by fluorous mixture synthesis

Organic Letters

Volumn 4, Issue 13, 2002, Pages 2233-2235

  Curran, Dennis P ^a   Furukawa, Takashi ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; ANTINEOPLASTIC AGENT; CARBAMIC ACID DERIVATIVE; DISCODERMOLIDE; FLUORINATED HYDROCARBON; FLUORINE; LACTONE; PYRONE DERIVATIVE;

ARTICLE; CHEMISTRY; CHROMATOGRAPHY; ISOLATION AND PURIFICATION; SYNTHESIS;

ALKANES; ANTINEOPLASTIC AGENTS; CARBAMATES; CHROMATOGRAPHY; FLUORINE; HYDROCARBONS, FLUORINATED; LACTONES; PYRONES;

EID: 0037182696     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026084t     Document Type: Article

References (22)

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6. Curran, D. P. Synlett 2001, 1488.
7. Leading references for prior synthetic work: (a) Nerenberg, J. B.; Hung, D. T.; Somers, P. K.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 12621.
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13. FPMB bromides.
14. Hoffmann, R. W. Angew. Chem., Int. Ed. 2000, 39, 2055.
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18. See Supporting Information for syntheses of precursors 5 and 8.
19. Mixture yields are calculated on the basis of average molecular weights. For example, the theoretical quantity of M-16 at 100% yield was calculated in the following manner: mmol expected x [(MW 16a + 16b + 16c +16d)/4].
20. Demixing was conducted on a Fluophase-RP column with the following gradient: from 80% MeOH/water to 100% MeOH over 30 min and then to 90% MeOH/10% THF over 15 min. Retention times (min) were 17.3, 22.5, 28.1, and 30.1.
21. 13 tag was isolated during demixing and tentatively assigned as the (21E)-diene by LC MS and LC NMR. The estimated overall yield of this product is 3-4%; however, we were not able to purify and characterize the expected (E)-isomer of 2b after detagging.
22. Minguez, J.; Curran, D. P., unpublished results.