Tin triflate promoted synthesis of bicyclic and tricyclic sulfonyl dihydropyrans

被引：10
|
作者：
Chan, Chieh-Kai [1 ]
Chen, Yu-Hsin [1 ]
Chang, Meng-Yang [1 ]
机构：
[1] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 807, Taiwan
来源：
TETRAHEDRON | 2016年 / 72卷 / 33期
关键词：
Tin triflate; beta-Ketosulfones; Carbocyclization; Dihydropyrans; ENANTIOSELECTIVE TOTAL-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; AEROBIC OXYSULFONYLATION; BIOMIMETIC CYCLIZATION; ALPHA-ARYLATION; ACID; SQUALENE; REARRANGEMENT; BIOSYNTHESIS; (+/-)-AMBROX;
D O I：
10.1016/j.tet.2016.07.009
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Tin triflate-promoted one-pot intramolecular annulation of alpha-geranyl or alpha-farnesyl beta-ketosulfones 3-4 affords the respective bicyclic or tricyclic sulfonyl dihydropyrans 5-6 in moderate to good yields via a cascade cation-olefin-carbonyl carbocyclization process. The starting materials 3 and 4 were obtained by K2CO3-mediated alpha-geranylation or alpha-farnesylation of beta-ketosulfones 1 with bromides 2a or 2b. The structures of the key products were confirmed by X-ray crystallography. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5121 / 5131
页数：11
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