Synthetic studies on d-biotin, part 9.: An improved asymmetric synthetic route to d-biotin via Hoffmann-Roche lactone-thiolactone approach

被引：17

作者：

Chen, FE ^{[1
]}

Jia, HQ

Chen, XX

Da, HF

Xie, B

Kuang, YY

Zhao, JF

机构：

[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China

[2] Shenyang Pharmaceut Univ, Sch Pharmaceut Engn, Shenyang 110016, Peoples R China

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2005年 / 53卷 / 07期

关键词：

d-biotin; vitamin H; polymer-supported oxazaborolidine; asymmetric reduction; Wittig reaction; desymmetrization;

D O I：

10.1248/cpb.53.743

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

An efficient and highly stereoselective total synthesis of d-biotin has been achieved starting from cis-1,3-dibenzyl-2-imidazolidone-4,5-dicarboxylic acid (2) with an overall yield of 33%. Polymer-supported oxazaborolidine-catalyzed asymmetric reduction of meso-cyclic imide 4 constitutes the key synthetic step in introducing stereogenic centers into the d-biotin molecule.

引用

页码：743 / 746

页数：4

共 3 条

[1] Synthetic studies on d-biotin, part 8:: An efficient chemoenzymatic approach to the asymmetric total synthesis of d-biotin via a polymer-supported PLE-mediated desymmetrization of meso-symmetic dicarboxylic esters
Chen, FE
Chen, XX
Dai, HF
Kuang, YY
Xie, B
Zhao, JF
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (04) : 549 - 554
[2] Synthetic studies on d-biotin.: Part 7:: A practical asymmetric total synthesis of d-biotin via enantioselective reduction of meso-cyclic imide catalyzed by oxazborolidine
Chen, FE
Dai, HF
Kuang, YY
Jia, HQ
TETRAHEDRON-ASYMMETRY, 2003, 14 (23) : 3667 - 3672
[3] Synthetic studies on d-biotin, part 6:: An expeditious and enantiocontrolled approach to the total synthesis of d-biotin via a polymer-supported chiral oxazaborolidine-catalyzed reduction of meso-cyclic imide strategy
Chen, FE
Yuan, JL
Dai, HF
Kuang, YY
Chu, Y
SYNTHESIS-STUTTGART, 2003, (14): : 2155 - 2160

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