Diastereoselective Synthesis of Tetrahydrofurano[2,3-g]indolizidines and 8-Aminoindolizidines from L-Asparagine

被引：1

作者：

Kuntiyong, Punlop ^{[1
]}

Inprung, Nantachai ^{[1
]}

Attanonchai, Sineenart ^{[1
]}

Kheakwanwong, Wichita ^{[1
]}

Bunrod, Pijitra ^{[1
]}

Akkarasamiyo, Sunisa ^{[1
]}

机构：

[1] Silpakorn Univ, Fac Sci, Dept Chem, Sanamchandra Palace 73000, Muang Nakhon Pa, Thailand

来源：

SYNLETT | 2022年 / 33卷 / 14期

关键词：

diastereoselective synthesis; aminoindolizidines; tandem cyclization; furanoindolizidines; asparagine; ACYLIMINIUM ION CYCLIZATION; INDOLIZIDINE ALKALOIDS;

D O I：

10.1055/a-1806-6089

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

8-Aminoindolizidines were synthesized from L-asparagine as the chiral starting material. The key dibenzylamino succinimide intermediate was synthesized in two steps. Three homologs of chiral hydroxy lactams tethered with hydroxyalkenes were synthesized from the succinimide through a sequence involving N-alkylation, cross-olefin metathesis, and hydride reduction. The dibenzylamino group gave stereocontrol of the key N-acyliminium ion cyclization of these hydroxy lactams. 5-Substituted aminoindolizidines were synthesized with high diastereoselectivity at C6. A tandem cyclization of an N-(6-hydroxyhex-3-en-1-yl) gamma-hydroxy lactam resulted in the formation of a tetrahydrofurano[2,3-g]indolizidine system.

引用

页码：1377 / 1382

页数：6

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