First total synthesis of (-)-diospongin B
First total synthesis of (-)-diospongin B
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DOI：
10.1016/j.tetlet.2005.10.129
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发表时间：
2006-01-02
影响因子：
1.8
通讯作者：
Jagadeesh, B
中科院分区：
文献类型：
--
作者：
Chandrasekhar, S;Shyamsunder, T;Jagadeesh, B
采用三组分偶联法，由相应的乙酰化Baylis-Hillman加合物、叠氮化钠和末端炔合成了一系列1，4-二取代-1，2，3-三唑。这种一锅法反应进一步提高了“点击”合成的效率，并使多官能1，4-二取代-1，2，3-三唑的制备多样化。(c)2006 Elsevier Ltd.保留所有权利。首次以苯甲醛为起始原料，通过手性烯丙基化、碱催化的α，β-不饱和酯的共轭加成和分子内氧-迈克尔反应实现了（-）-diospongin B的全合成，总收率为16%。(c)2005爱思唯尔有限公司保留所有权利。
A three-component coupling was used to prepare a series of 1,4-disubstituted-1,2,3-triazoles from the corresponding acetylated Baylis-Hillman adducts, sodium azide and terminal alkynes. This one-pot reaction further increases the efficacy of 'Click' synthesis and diversifies the preparation of multi-functional 1,4-disubstituted-1,2,3-triazoles. (c) 2006 Elsevier Ltd. All rights reserved.The first total synthesis of (-)-diospongin B has been achieved starting from benzaldehyde using chiral allylation, a base catalyzed conjugate addition of an alpha,beta-unsaturated ester and an intramolecular oxy-Michael reaction as the key steps in 16% overall yield. (c) 2005 Elsevier Ltd. All rights reserved.