Synthetic studies on nemorosone via enantioselective intramolecular cyclopropanation

被引：28
作者：
Abe, Masahito
Saito, Aya
Nakada, Masahisa [1 ]
机构：
[1] Waseda Univ, Fac Sci & Engn, Dept Chem, Shinjuku Ku, Tokyo 1698555, Japan
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 09期
关键词：
BETA-KETO SULFONES; POLYCYCLIC POLYPRENYLATED ACYLPHLOROGLUCINOLS; 2 POLYISOPRENYLATED BENZOPHENONES; PHLOROGLUCIN NATURAL-PRODUCTS; ALPHA-DIAZOCARBONYL COMPOUNDS; ASYMMETRIC TOTAL-SYNTHESIS; GARSUBELLIN-A SYNTHESIS; HYPERICUM-PERFORATUM; ORGANIC-SYNTHESIS; REGIOSELECTIVE LITHIATION;
D O I：
10.1016/j.tetlet.2009.12.147
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
This Letter describes synthetic studies of nemorosone via enantioselective intramolecular cyclopropanation. For the total synthesis of nemorosone, three potential intermediates were evaluated through the efficiency of three sequential reactions, namely, their intramolecular cyclopropanation, dimethylation of the resultant cycloproparies, and ring-opening reaction of the alkylated cyclopropanes. As a result, alpha-diazomethyl ketone 10c was found to be the most suitable. The enantroselective intramolecular cyclopropanation to construct the bicyclo[3 3 1]nonane core and preparation of the compound with all the correct stereogenic centers of nemorosone are also described. (C) 2010 Elsevier Ltd All rights reserved.
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页码：1298 / 1302
页数：5
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