Synthesis of a ceramide sphingolipid as a potential sex pheromone of the hair crab Erimacrus isenbeckii using butane-2,3-diacetal desymmetrised glycolic acid building blocks

被引：21

作者：

Dixon, DJ ^{[1
]}

Ley, SV ^{[1
]}

Lohmann, S ^{[1
]}

Sheppard, TD ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

SYNLETT | 2005年 / 03期

关键词：

acetals; chiral auxiliaries; pheromones; sphingolipids; stereoselective synthesis;

D O I：

10.1055/s-2005-862361

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective synthesis of a ceramide sphingolipid as a potential sex pheromone of the hair crab Erimacrus isenbeckii is reported using diastereoselective alkylation and aldol reactions of butane-2,3-diacetal (BDA) desymmetrised glycolic acid building blocks as the key synthetic steps.

引用

页码：481 / 484

页数：4

共 24 条

[1] Sex pheromones of the hair crab EP Erimacrus isenbeckii.: Part 1:: Isolation and structures of novel ceramides
Asai, N
Fusetani, N
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[J]. TETRAHEDRON, 2000, 56 (51) : 9895 - 9899
[2] Sex pheromones of the hair crab Erimacrus isenbeckii.: II.: Synthesis of ceramides
Asai, N
Fusetani, N
Matsunaga, S
[J]. JOURNAL OF NATURAL PRODUCTS, 2001, 64 (09): : 1210 - 1215
[3] The use of butane diacetals of glycolic acid as precursors for the synthesis of the phytotoxic calmodulin inhibitor herbarumin II
Díez, E
Dixon, DJ
Ley, SV
Polara, A
Rodríguez, F
[J]. HELVETICA CHIMICA ACTA, 2003, 86 (11) : 3717 - 3729
[4] Diez E, 2003, SYNLETT, P1186
[5] Díez E, 2001, ANGEW CHEM INT EDIT, V40, P2906, DOI 10.1002/1521-3773(20010803)40:15<2906::AID-ANIE2906>3.0.CO
[6] 2-5
[7] Dixon DJ, 2001, ANGEW CHEM INT EDIT, V40, P4763, DOI 10.1002/1521-3773(20011217)40:24<4763::AID-ANIE4763>3.0.CO
[8] 2-D
[9] Dixon DJ, 2002, SYNTHESIS-STUTTGART, P1973
[10] Highly diastereoselective lithium enolate aldol reactions of butane-2,3-diacetal desymmetrized glycolic acid and deprotection to enantiopure anti-2,3-dihydroxy esters
Dixon, DJ
Ley, SV
Polara, A
Sheppard, T
[J]. ORGANIC LETTERS, 2001, 3 (23) : 3749 - 3752

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