An asymmetric synthesis of the γ-amino-β-hydroxy acid segment of hapalosin

被引：7

作者：

Mula, S ^{[1
]}

Chattopadhyay, S ^{[1
]}

机构：

[1] Bhabha Atom Res Ctr, Bioorgan Div, Bombay 400085, Maharashtra, India

来源：

LETTERS IN ORGANIC CHEMISTRY | 2006年 / 3卷 / 01期

关键词：

gamma-amino-beta-hydroxy acid; asymmetric synthesis; (R)-cyclohexylidene glyceraldehyde; hapalosin;

D O I：

10.2174/157017806774964468

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile synthesis of the title compound has been developed starting from a homoallylic alcohol that can be conveniently prepared from (R)-cyclohexylidene glyceraldehyde. The key features of the synthesis were its operational simplicity and the use of inexpensive compounds.

引用

页码：54 / 55

页数：2

共 29 条

[11] Total synthesis of hapalosin and two ring expanded analogs [J].

Hermann, C ;

Pais, GCG ;

Geyer, A ;

Kühnert, SM ;

Maier, ME .

TETRAHEDRON, 2000, 56 (43) :8461-8471

[12]

Huang PQ, 2003, CHINESE J CHEM, V21, P723

[13] An easy access to protected (4S, 5R)-5-Alkyl-4-hydroxy-2-pyrrolidinones and their use as versatile synthetic intermediates [J].

Huang, PQ ;

Wang, SL ;

Ye, JL ;

Ruan, YP ;

Huang, YQ ;

Zheng, H ;

Gao, JX .

TETRAHEDRON, 1998, 54 (41) :12547-12560

[14] Ketoreductases in the synthesis of valuable chiral intermediates:: application in the synthesis of α-hydroxy β-amino and β-hydroxy γ-amino acids [J].

Kambourakis, S ;

Rozzell, JD .

TETRAHEDRON, 2004, 60 (03) :663-669

[15] Synthesis of the γ-amino-β-hydroxy acid of hapalosin via an asymmetric dihydroxylation route [J].

Maier, ME ;

Hermann, C .

TETRAHEDRON, 2000, 56 (04) :557-561

[16] Synthetic study on hapalosin, a cyclic depsipeptide possessing multidrug resistance reversing activities [J].

Ohmori, K ;

Okuno, T ;

Nishiyama, S ;

Yamamura, S .

TETRAHEDRON LETTERS, 1996, 37 (20) :3467-3470

[17] Chemical study on hapalosin, a cyclic depsipeptide possessing multidrug resistance reversing activities: Synthesis, structure and biological activity [J].

Okuno, T ;

Ohmori, K ;

Nishiyama, S ;

Yamamura, S ;

Nakamura, K ;

Houk, KN ;

Okamoto, K .

TETRAHEDRON, 1996, 52 (47) :14723-14734

[18]

Oshitari T, 2004, HETEROCYCLES, V62, P185

[19] Efficient synthesis of the γ-amino-β-hydroxy acid subunit of hapalosin [J].

Pais, GCG ;

Maier, ME .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4551-4554

[20] A practical total synthesis of hapalosin, a 12-membered cyclic depsipeptide with multidrug resistance-reversing activity, by employing improved segment coupling and macrolactonization [J].

Palomo, C ;

Oiarbide, M ;

García, JM ;

González, A ;

Pazos, R ;

Odriozola, JM ;

Bañuelos, P ;

Tello, M ;

Linden, A .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (12) :4126-4134

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