A simple and novel synthesis of (+)-monocerin was achieved in 15 steps and 15.5% overall yield from 3-buten-1-ol employing hydrolytic kinetic resolution, Julia olefination, intramolecular tandem Sharpless asymmetric dihydroxylation-SN2 cyclization and a novel copper mediated tandem cyanation-cyclization as the key steps.
aThe total synthesis of (+)-petromyroxol, a tetrahydrofuran (THF)-diol fatty acid, isolated from sea lamprey larvae (Petromyzon marinus) is reported. The present synthesis employs a tandem α-aminoxylation-allylation, cross metathesis and tandem asymmetric dihydroxylation-SN2 cyclization as key steps.
A straightforward and highly selective method has been developed for the nitration of a wide variety of aromatic and aliphatic olefins by using a clay-supported copper nitrate (Claycop) and a catalytic amount of (2,2,6,6-tetramethylpiperidin-1-yl)oxyl, an inexpensive and mild reagent system. High conversions and exclusive E-selectivity, together with the environmentally benign nature of the Claycop reagent, make this a green method and an attractive alternative to established methods.
A simple and highly efficient method has been developed for the regioselective sulfenylation of a wide variety of indoles with alkyl and aryl sulfonylhydrazides as a sulphur source and CeCl3⋅7H2O‐NaI as an inexpensive and readily available reagent system. This method involves the breaking of sulfur–oxygen and sulfur–nitrogen bonds and making of carbon‐sulfur bond. The method provides high yields of the products with enhanced regioselectivity. We studied the reactivity of various electron rich and electron deficient indoles towards the sulfenylation reaction. The indoles containing electron donating group reacts fast towards the sulfenylation reaction as compared to the indoles containing electron withdrawing groups. More over functional groups like alkoxy, aryloxy, bromo, nitro, cyano, ester, were well tolerated under the established reaction conditions. We also proposed a plausible mechanism for this transformation. The experimental simplicity and environmentally benign nature of the reagent system makes this method an attractive alternative to established methods.
The first enantioselective total synthesis of seimatopolide B has been achieved, using ring-closing metathesis and DCC (N,N9-dicyclohexylcarbodiimide) coupling as key steps. The stereogenic centres were generated by means of iterative hydrolytic kinetic resolution (HKR) of racemic epoxides.
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