@phdthesis{oai:nagoya.repo.nii.ac.jp:00010569, author = {佐藤, 恒夫 and Sato, Tsuneo}, month = {Apr}, note = {The stereocontrolled, general synthesis of C-nucleosides starting from inexpensive non-carbohydrate substances has been accomplished. Construction of' the ribose skeleton, a key operation,relies on the efficiency of the [3 + 4] cyclocoupling reaction between polybromo ketones and furans aided by low-valent transition metals which leads to 8-oxabicyclo[3.2.1]octan-3-one structures. Pseudouridine and its analogues such as 2-thiopseudouridine,pseudoisocytidine, 6-azapseudouridine, and 6-aza-2-thiopseudouridine have been synthesized from (1R,6S,7S,8R)-7,8-isopropylidenedioxy-3,9-dioxabicyclo[4.2.l^l,6]nonan-4-one. Showdomycin is also obtainable from the common intermediate. A variety of pyrimidine C-nucleosides bearing branched-chain sugars have been synthesized starting from adequately substituted (lR*,6S*,7S*,8R*)-7,8-isopropylidenedioxy-3,9- dioxabicyclo[4.2.1^1,6]nonan-4-ones in only three steps. In addition, the straightforward synthesis of homo-C-nucleosides has been achieved, which allows the synthesis of homopseudouridine, homoshowdomycin, homopyrazomycin, etc., 名古屋大学博士学位論文 学位の種類 : 理学博士(課程) 学位授与年月日 : 昭和58年4月30日}, school = {名古屋大学, Nagoya University}, title = {C-ヌクレオシドの一般合成法}, year = {1983} }