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. 2012 Jan 6;14(1):426-8.
doi: 10.1021/ol203161u. Epub 2011 Dec 7.

Total synthesis of (-)-tirandamycin C

Ming Chen  1 , William R Roush
Affiliations

Total synthesis of (-)-tirandamycin C

Ming Chen et al. Org Lett. .

Abstract

Tirandamycin C is a newly isolated member of the tetramic acid family natural products. We described herein the first enantioselective synthesis of natural (-)-tirandamycin C, the postulated biosynthetic precursor of other members of this family. The highly stereoselective (>15:1) mismatched double asymmetric γ-stannylcrotylboration reaction of aldehyde 8 with crotylborane reagent (R)-E-9 was utilized to access the key anti,anti-stereotriad 18.

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Figures

Figure 1
Figure 1
Tetramic acid containing natural products, tirandamycins A–D
Scheme 1
Scheme 1
Tirandamycin C, retrosynthetic analysis
Scheme 2
Scheme 2
Total synthesis of (−)-tirandamycin C (1)
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