Reference

Synthesis of the C-glycoside of methyl a-D-altropyranosyl-(1?4)-a-D-glucopyranoside

Synthesis of the C-glycoside of methyl a-D-altropyranosyl-(1?4)-a-D-glucopyranoside. Denton, Richard W.; Mootoo, David R. (Department of Chemistry, Hunter College, New York, NY, USA). Journal of Carbohydrate Chemistry, 22(7 & 8), 671-683 (English) 2003 Marcel Dekker, Inc. CODEN: JCACDM. ISSN: 0732-8303. DOCUMENT TYPE: Journal CA Section: 33 (Carbohydrates) The C-glycoside of Me a-D-altropyranosyl-(1?4)-a-D-glucopyranoside was prepd.There are some commonly used reagents with their cas registry numbers 13199-25-2 and 652991-33-8 in this article. in a convergent fashion, from readily available precursors, 4-O-tert-butyl-diphenylsilyl-1,2-O-isopropylidene-D-erythro-S-Ph monothiohemiacetal (five steps from D-ribose) and the known acid, Me 2,3,6-tri-O-benzyl-4-C-(carboxy-methyl)-4-deoxy-a-D-glucopyranoside (seven steps from Me a-D-glucopyranoside). The key reactions in the synthesis are the oxocarbenium ion cyclization of thioacetal-enol ethers to a C1 substituted glycal, and the stereoselective hydroboration of the glycal to the a-C-altroside. .

Stereoselective benzylic a-acylamino radical cyclization: a model study for the Tacaman indole alkaloid skeleton

Stereoselective benzylic a-acylamino radical cyclization: a model study for the Tacaman indole alkaloid skeleton. Clauss, Rainer; Hunter, Roger (Dep. Chem., Univ. Cape Town, Rondebosch 7700, S. Afr.). Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry, (1), 71-76 (English) 1997 Royal Society of Chemistry. CODEN: JCPRB4. ISSN: 0300-922X. DOCUMENT TYPE: Journal CA Section: 31 (Alkaloids) Section cross-reference(s): 33 Radical cyclization with tributyltin hydride of the a-phenylsulfanyl lactam I, prepd. 186968-95-6 and 13199-25-2 which are cas registry numbers of chemicals are mentioned. in nine steps from D-ribose via the corresponding phthalimide, gives the all-cis tetrahydropyrido[2,1-a]isoindolone II stereoselectively as the major diastereomer. The structure of the product is established by 1H NMR spectroscopy and corroborated by formation of the cis-lactone III. The diastereoselectivity is shown to be controlled by the allylic/homoallylic cis-ketal group, and a transition state is proposed. The sequence constitutes the first simple model study for C/D ring fusion of the tacaman indole alkaloid skeleton via the relatively unexplored C-3-C-14 bond disconnection. .