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Intramolecular reaction
About: Intramolecular reaction is a research topic. Over the lifetime, 5015 publications have been published within this topic receiving 138213 citations.
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TL;DR: The reaction of rapamycin and FK506 with n -Bu 4 N + CN − / aq results in an efficient excision of their pipecolinate subunits, leading in good yields to compounds 3 and 12 , respectively.
40 citations
TL;DR: In this article, photolysis of 3β-methoxymethoxy-5α-cholestan-6β-ylcyanamide (6), 29methoxyfriedelan-3 β-yl-cyanamides (15), (22R,25R)-5α-, 5α-furostan-26-ylcyclic-cyclicamide (23), 8α,12-(12R/12S)-epoxylabdan-15-ylamides, (32) and (33)
Abstract: Photolysis of 3β-methoxymethoxy-5α-cholestan-6β-ylcyanamide (6), 29-methoxyfriedelan-3β-yl-cyanamide (15), (22R,25R)-5α-furostan-26-ylcyanamide (23), 8α,12-(12R/12S)-epoxylabdan-15-ylcyanamides, (32) and (33), in the presence of iodine and lead tetra-acetate leads to neutral cyanimyl radicals which undergo intramolecular hydrogen abstraction to produce N-cyanoepimino compounds. Better results are obtained with the system iodine and diacetoxyiodobenzene. The starting cyanamides have been prepared by reduction of the oximes (3) and (13) and of the amides (20), (28), and (29), respectively, with lithium aluminium hydride followed by cyanation with cyanogen bromide or with sodium cyanate and subsequent dehydration of the urea derivative with methanesulphonyl chloride.
40 citations
TL;DR: This initial total synthesis of an asbestinin also serves to confirm the absolute configuration of this subclass of the C-2-C-11-cyclized cembranoid natural products.
Abstract: A highly stereoselective synthesis of 11-acetoxy-4-deoxyasbestinin D (1) has been completed in 26 linear steps. The synthesis hinges on a selective glycolate aldol addition to establish the C-2 stereocenter, a ring-closing metathesis reaction to complete the oxonene, and an intramolecular Diels−Alder cycloaddition to establish the relative configuration at C-1, C-10, and C-14. This initial total synthesis of an asbestinin also serves to confirm the absolute configuration of this subclass of the C-2−C-11-cyclized cembranoid natural products.
40 citations
40 citations
TL;DR: In this paper, a variety of polycyclic quinolines were synthesized in two steps by an initial reductive cyclization followed by another intramolecular cyclization in the allylamines afforded from either the acetates or allyl bromides of Baylis-Hillman adducts of 2-nitrobenzaldehydes and acrylonitrile.
40 citations