✍ Scribed by Daniel Romo; Robert M. Rzasa; Helene A. Shea; Kaapjoo Park; Joseph M. Langenhan; Luo Sun; Alexander Akhiezer; Jun O. Liu
No coin nor oath required. For personal study only.
Total Synthesis of Immunosuppressive Activity of (-)-Pateamine A and Related Compounds: Implementation of a β-Lactam-Based Macrocyclization.
-The key step of the convergent, stereoflexible route to pateamine A (X) and derivatives is based on the macrocyclization of β-lactam (IV). The use of NEt 4 CN as CH 2 Cl 2 -soluble source of cyanide ions greatly simplifies the product (V) isolation. The Stille coupling of bromide (VII) with stannane (VIII) proceeds competitively with π-allyl formation to append the trienylamine side chain on the macrocycle. Because the deprotection of the Boc-protected title compound proceeds with decomposition the 2,2,2-trichloro-1,1-dimethylethoxycarbonyl group is found as suitable amino protecting group. IC 50 values are determined for synthetic and natural pateamine A and related compounds in the interleukin 2 reporter gene assay. -(ROMO, DANIEL;
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