Concise synthesis of the C-1-C-12 fragment of amphidinolides T1-T5

被引：15

作者：

Clark, J. Stephen ^{[1
]}

Labre, Flavien ^{[1
]}

Thomas, Lynne H. ^{[1
]}

机构：

[1] Univ Glasgow, Sch Chem, WestCHEM, Glasgow G12 8QQ, Lanark, Scotland

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 13期

关键词：

DINOFLAGELLATE AMPHIDINIUM SP; CONVERGENT TOTAL-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; 19-MEMBERED MACROLIDE; OLEFIN METATHESIS; OXONIUM YLIDES; T1; REARRANGEMENT; T4;

D O I：

10.1039/c1ob05130j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The C-1-C-12 segment of the amphidinolides T1-T5 has been synthesised in an efficient manner. The key transformations are highly diastereoselective rearrangement of an oxonium ylide, or metal-bound ylide equivalent, produced by intramolecular reaction of a copper carbenoid with an allylic ether, and macrocyclic fragment coupling by one-pot ring-closing metathesis and hydrogenation.

引用

页码：4823 / 4830

页数：8

共 29 条

[21] Amphidinolides T2, T3, and T4, new 19-membered macrolides from the dinoflagellate Amphidinium sp and the biosynthesis of amphidinolide T1
Kobayashi, J
Kubota, T
Endo, T
Tsuda, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) : 134 - 142
[22] Amphidinolide T5, a new 19-membered macrolide from a dinoflagellate and X-ray structure of amphidinolide T1
Kubota, T
Endo, T
Tsuda, M
Shiro, M
Kobayashi, J
[J]. TETRAHEDRON, 2001, 57 (29) : 6175 - 6179
[23] A Concise Total Synthesis of Amphidinolide T2
Li, Huoming
Wu, Jinlong
Luo, Jialu
Dai, Wei-Min
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (38) : 11530 - 11534
[24] Tandem catalysis: The sequential mediation of olefin metathesis, hydrogenation, and hydrogen transfer with single-component Ru complexes
Louie, J
Bielawski, CW
Grubbs, RH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (45) : 11312 - 11313
[25] 4-DIALKYLAMINOPYRIDINES AS ACYLATION CATALYSTS .5. SIMPLE METHOD FOR ESTERIFICATION OF CARBOXYLIC-ACIDS
NEISES, B
STEGLICH, W
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (07): : 522 - 524
[26] BINAP - AN EFFICIENT CHIRAL ELEMENT FOR ASYMMETRIC CATALYSIS
NOYORI, R
TAKAYA, H
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1990, 23 (10) : 345 - 350
[27] Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands
Scholl, M
Ding, S
Lee, CW
Grubbs, RH
[J]. ORGANIC LETTERS, 1999, 1 (06) : 953 - 956
[28] Amphidinolide T, novel 19-membered macrolide from marine dinoflagellate Amphidinium sp.
Tsuda, M
Endo, T
Kobayashi, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) : 1349 - 1352
[29] Stereoselective Synthesis of Amphidinolide T1
Yadav, J. S.
Reddy, Ch. Suresh
[J]. ORGANIC LETTERS, 2009, 11 (08) : 1705 - 1708

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