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Total synthesis
About: Total synthesis is a research topic. Over the lifetime, 25578 publications have been published within this topic receiving 489319 citations.
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TL;DR: The synthesis features an efficient cross-metathesis, an enzymatic kinetic resolution of a beta-hydroxy ester, a selective removal of a Boc-protecting group, a HATU/HOAt-promoted cycloamidation reaction, and synthetic manipulations to a sensitive thioester functional group.
95 citations
TL;DR: The synthesis of human insulin, a two-chain peptide containing three disulfide bonds, was achieved unambiguously by sequential and selective formation in the protein for the first time as mentioned in this paper.
Abstract: Total synthesis of human insulin, a two:chain peptide containing three disulfide bonds, was achieved unambiguously by sequential and selective formation of disulfide bonds in the protein for the first time. The key reaction in the synthesis is separate regioselective formation of three disulfide bonds using a silyl chloride method developed by us. Prior to the insulin synthesis, it was confirmed by the syntheses of double-disulfide peptides, conotoxin M1, β-hANP, and an unnatural parallel dimer of α-hANP, that no disulfide exchange occurred during the silyl chloride treatment. Using three orthogonal thiol-protecting groups, Trt, Acm, and t-Bu, the three disulfide bonds of human insulin were efficiently constructed by successive reactions using thiolysis, iodine oxidation, and the silyl chloride method
95 citations
95 citations
TL;DR: The total synthesis of naphthoquinone natural products isolated from the Bignoniaceae plant family is described and the first case of catalysis in oxa 6pi electrocyclizations is reported.
Abstract: The total synthesis of naphthoquinone natural products isolated from the Bignoniaceae plant family is described. Pinnatal, isopinnatal, sterekunthals A and B, pyranokunthones A and B, and anthrakunthone have been prepared along the lines of a biosynthetic proposal involving pericyclic reactions as key steps. The first case of catalysis in oxa 6π electrocyclizations is reported.
95 citations
TL;DR: In this paper, a solution of pyrimido[5,4g]pteridine N-oxide 1 (5 X M ) in MeCN was irradiated by using a grating monochromator (JASCO Model CRM-FA) with 2-kW Xe lamp and 4-nm band width under argon atmosphere for 2 h.
Abstract: Figure 1. (a) UV-visible absorption spectrum of pyrimido[5,4-g]pteridine N-oxide 1 (5 X M ) in MeCN. (b) Difference spectrum of the mixture of 1 (5 m M ) and D M A (250 m M ) vs. 1 (5 m M ) in MeCN. (c) Wavelength dependence (presented by the yield of M M A ) in the photochemical demethylation of D M A by 1. A solution of 1 (5 m M ) and D M A (50 m M ) in MeCN was irradiated by using a grating monochromator (JASCO Model CRM-FA) with 2-kW Xe lamp and 4-nm band width under argon atmosphere for 2 h.
95 citations