Synthesis of the C1-C5 and C6-C24 fragments of the RNA polymerase inhibitors ripostatin A and B

Synlett

Volumn , Issue 3, 2006, Pages 419-422

  Kujat, Christof ^a   Bock, Martin ^a   Kirschning, Andreas ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

Antibiotics; Nagao aldol reaction; Natural product synthesis; RNA polymerase inhibitors; Vinylogous aldol reaction

Indexed keywords

ANTIBIOTIC AGENT; RIPOSTATIN A; RIPOSTATIN B; RNA POLYMERASE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 33344459154     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926263     Document Type: Article

References (12)

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7. Denmark, S. E.; Beutner, G. L. J. Am. Chem. Soc. 2003, 125, 7800.
8. The pivaloate protection was beneficial for high diastereoselectivity (dr = 93:7). In contrast, the corresponding TBS-protected aldehyde gave the vinylogous aldol product in only 4:1 dr.
9. (a) The configuration of the newly formed stereogenic center was further proven for acetonide 17 according to Rychnovsky et al. Acetonide 17 was prepared after DIBAL-H reduction of 8 followed by protection of the 1,3-diol moiety (Figure 2). See: Rychnovsky, S. D.; Rogers, B. N.; Richardson, T. I. Acc. Chem. Res. 1998, 31, 9.
10. 3): δ = -4.5, -4.0, 16.3, 16.9, 18.1, 20.1, 25.9, 30.3, 34.1, 34.3, 36.5, 37.5, 44.3, 46.3, 59.3, 65.7, 67.4, 68.1, 98.4, 123.1, 125.7, 125.8, 2 × 128.3, 136.0, 136.4, 141.7 ppm.
11. -: 723.4629; found: 723.4622.
12. Ma, S.; Lu, X. J. Chem. Soc., Chem. Commun. 1990, 1643.