Total syntheses of CP-225,917 and CP-263,114: Creation of a matrix structure by sequential aldol condensation and intramolecular Heck ring closure

Angewandte Chemie - International Edition

Volumn 37, Issue 13-14, 1998, Pages 1877-1880

  Kwon, Ohyun ^a   Su, Dai Shi ^b   Meng, Dongfang ^a,b   Deng, Wei ^b   D'Amico, Derin C ^a   Danishefsky, Samuel J ^a,b  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

Aldol reactions; Heck reactions; Natural products; Synthetic methods

Indexed keywords

EID: 0032479724     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980803)37:13/14<1877::AID-ANIE1877>3.0.CO;2-2     Document Type: Article

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22. Early in our studies we conducted the same sort of aldol condensation of furan 16 (i.e., with 9 having a MOM rather than a PMB protecting group). The major product (ca. 83 %) corresponded to 17 (with MOM instead of PMB). However, the three other aldol products were also obtained (combined yield ca. 12%), each in homogeneous form following chromotography. In the case of 17, we could not find the corresponding minor products. This may reflect a subtle and unrecognized difference in experimental conditions. Alternatively, the difference may arise from a small sensitivity of the stereochemistry of the aldol reaction to the nature of the protecting group in the side chain at C4.
23. In parallel experiments, the Heck reaction of the unprotected alcohol was also accomplished, but in much lower yield and with poor reproducibility. For another instance of the power of the sequential Heck-Aldol logic, see reference [15].
24. [15] and by Sharpless catalytic methods (M. A. Warpehoski, B. Chabaud, K. B. Sharpless, J. Org. Chem. 1982, 47, 2897). However, the experiments shown here provided the best results.
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