Synthesis, structure revision, and absolute configuration of (+)-didemniserinolipid B, a serinol marine natural product from a tunicate Didemnum sp.

被引：56

作者：

Kiyota, H

Dixon, DJ

Luscombe, CK

Hettstedt, S

Ley, SV

机构：

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

[2] Tohoku Univ, Grad Sch Agr Sci, Aoba Ku, Sendai, Miyagi 9818555, Japan

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 19期

关键词：

D O I：

10.1021/ol026421y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

En route to proving the absolute and relative stereochemistry, through synthesis, of (+)-didemniserinolipid B (1), the first natural serinolipid isolated from a tunicate Didemnum sp., it was discovered that the isolated natural product was in fact the 31-sulfate configured 8R,9R,10R,13S,30S. This structural reassignment was only possible after the development of a microwave-assisted method for the sulfation of unreactive hydroxyl groups.

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页码：3223 / 3226

页数：4

相关论文

共 19 条

[1] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].

BLANCHETTE, MA ;

CHOY, W ;

DAVIS, JT ;

ESSENFELD, AP ;

MASAMUNE, S ;

ROUSH, WR ;

SAKAI, T .

TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186

[2] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156

[3]

Dixon DJ, 2000, ANGEW CHEM INT EDIT, V39, P3622, DOI 10.1002/1521-3773(20001016)39:20<3622::AID-ANIE3622>3.0.CO

[4]

2-H

[5]

Dixon DJ, 2002, CHEM-EUR J, V8, P1621, DOI 10.1002/1521-3765(20020402)8:7<1621::AID-CHEM1621>3.0.CO

[6]

2-8

[7] Rapid assembly of anti,anti-1,2,3-triol motifs via stereoselective addition of organometallics to aldehydes obtained from (R′,R′,S,R)-2,3-butane diacetal protected butanetetraol derivatives [J].

Dixon, DJ ;

Krause, L ;

Ley, SV .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (20) :2516-2518

[8] A general and efficient procedure for the preparation of enantiopure anti-1,2-diols -: synthesis and utility of (R′,R′,S,R)-2,3-butane diacetal protected butane tetrol [J].

Dixon, DJ ;

Foster, AC ;

Ley, SV ;

Reynolds, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (12) :1635-1637

[9] Preparation of desymmetrised meso-tartrate derivatives -: synthesis and utility of (R′,R′,R,S)-2,3-butane diacetal protected dimethyl tartrate [J].

Dixon, DJ ;

Foster, AC ;

Ley, SV ;

Reynolds, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (12) :1631-1633

[10] A short and efficient stereoselective synthesis of the polyhydroxylated macrolactone (+)-aspicilin [J].

Dixon, DJ ;

Foster, AC ;

Ley, SV .

ORGANIC LETTERS, 2000, 2 (02) :123-125