A Concise Enantioselective Synthesis of the Chlorosulfolipid Malhamensilipin A

被引：55

作者：

Bedke, D. Karl ^{[1
]}

Shibuya, Grant M. ^{[1
]}

Pereira, Alban R. ^{[2
]}

Gerwick, William H. ^{[2
]}

Vanderwal, Christopher D. ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

[2] Univ Calif San Diego, Scripps Inst Oceanog, Ctr Marine Biotechnol & Biomed, La Jolla, CA 92093 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 08期

关键词：

CATALYTIC ASYMMETRIC DIHYDROXYLATION; OCHROMONAS-DANICA; ADRIATIC MUSSELS; STEREOCHEMISTRY; SHELLFISH; MOTIFS; LIPIDS; TOXINS;

D O I：

10.1021/ja910809c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first enantioselective synthesis of a member of the chlorosulfolipid family of natural products is reported. All of the polar substituents of malhamensilipin A are introduced with high stereoselectivity, and the unique (E)-chlorovinyl sulfate is created by a chemo-, regio-, and stereoselective E2 elimination of HCl in a reaction that likely has a counterpart in the biosynthesis of this fascinating natural product.

引用

页码：2542 / +

页数：3

共 24 条

[1] Relative Stereochemistry Determination and Synthesis of the Major Chlorosulfolipid from Ochromonas danica
Bedke, D. Karl
Shibuya, Grant M.
Pereira, Alban
Gerwick, William H.
Haines, Thomas H.
Vanderwal, Christopher D.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (22) : 7570 - +
[2] P-2-NICKEL CATALYST WITH ETHYLENEDIAMINE, A NOVEL SYSTEM FOR HIGHLY STEREOSPECIFIC REDUCTION OF ALKYNES TO CIS-OLEFINS
BROWN, CA
AHUJA, VK
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (15) : 553 - 554
[3] STRUCTURE OF MALHAMENSILIPIN-A, AN INHIBITOR OF PROTEIN-TYROSINE KINASE, FROM THE CULTURED CHRYSOPHYTE POTERIOOCHROMONAS-MALHAMENSIS
CHEN, JL
PROTEAU, PJ
ROBERTS, MA
GERWICK, WH
SLATE, DL
LEE, RH
[J]. JOURNAL OF NATURAL PRODUCTS, 1994, 57 (04): : 524 - 527
[4] A new cytotoxic polychlorinated sulfolipid from contaminated Adriatic mussels
Ciminiello, P
Dell'Aversano, C
Fattorusso, E
Forino, M
Magno, S
Di Meglio, P
Ianaro, A
Poletti, R
[J]. TETRAHEDRON, 2004, 60 (33) : 7093 - 7098
[5] Shellfish toxins - Chemical studies on northern Adriatic mussels
Ciminiello, P
Fattorusso, E
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (12) : 2533 - 2551
[6] Toxins from Adriatic blue mussels. A decade of studies
Ciminiello, P
Dell'Aversano, C
Fattorusso, E
Forino, M
Magno, S
[J]. PURE AND APPLIED CHEMISTRY, 2003, 75 (2-3) : 325 - 336
[7] Structure and stereochemistry of a new cytotoxic polychlorinated sulfolipid from Adriatic shellfish
Ciminiello, P
Dell'Aversano, C
Fattorusso, E
Forino, M
Magno, S
Di Rosa, M
Ianaro, A
Poletti, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) : 13114 - 13120
[8] Structural elucidation of a new cytotoxin isolated from mussels of the Adriatic sea
Ciminiello, P
Fattorusso, E
Forino, M
Di Rosa, M
Ianaro, A
Poletti, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (02) : 578 - 582
[9] A simple one-pot organometallic formylation/trapping sequence using N-formylcarbazole
Dixon, DJ
Lucas, AC
[J]. SYNLETT, 2004, (06) : 1092 - 1094
[10] A NEW CLASS OF LIPIDS - CHLOROSULFOLIPIDS
ELOVSON, J
VAGELOS, PR
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1969, 62 (03) : 957 - &

← 1 2 3 →