Studies of the Asymmetric Total Synthesis of Clavilactone D by the 'Lariat' Cyclization Strategy

被引：11

作者：

Yoshimitsu, Takehiko ^{[1
]}

Nojima, Shoji ^{[1
]}

Hashimoto, Masashi ^{[1
]}

Tsukamoto, Koji ^{[1
]}

Tanaka, Tetsuaki ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

SYNTHESIS-STUTTGART | 2009年 / 17期

关键词：

total synthesis; natural products; cyclizations; asymmetric synthesis; alkylations; ORGANIC-SYNTHESIS; STRUCTURE ELUCIDATION; RADICAL REACTIONS; INDIUM METAL;

D O I：

10.1055/s-0029-1216909

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A route to the core structure of clavilactone D, a new member of the tyrosine kinase inhibitors, is reported. The route employs sequential cyclization initiated by iodo etherification followed by Friedel-Crafts cyclization to furnish a polycyclic lactone fused with an aromatic ring, which is readily transformed into the proposed clavilactone scaffold.

引用

页码：2963 / 2969

页数：7

共 18 条

[1] [Anonymous], J CHEM SOC P1
[2] SECONDARY MOLD METABOLITES .47. ISOLATION AND STRUCTURE ELUCIDATION OF CLAVILACTONES AC, NEW METABOLITES FROM THE FUNGUS CLITOCYBE CLAVIPES
ARNONE, A
CARDILLO, R
MEILLE, SV
NASINI, G
TOLAZZI, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (15): : 2165 - 2168
[3] Clavilactones, a novel class of tyrosine kinase inhibitors of fungal origin
Cassinelli, G
Lanzi, C
Pensa, T
Gambetta, RA
Nasini, G
Cuccuru, G
Cassinis, M
Pratesi, G
Polizzi, D
Tortoreto, M
Zunino, F
[J]. BIOCHEMICAL PHARMACOLOGY, 2000, 59 (12) : 1539 - 1547
[4] Advances in indium-catalysed organic synthesis
Chauhan, KK
Frost, CG
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (18): : 3015 - 3019
[5] CINTAS P, 1995, SYNLETT, P1087
[6] Highly convergent three component benzyne coupling:: The total synthesis of ent-clavilactone B
Larrosa, Igor
Da Silva, Marianne I.
Gomez, Patricio M.
Hannen, Peter
Ko, Eunjung
Lenger, Steven R.
Linke, Simon R.
White, Andrew J. P.
Wilton, Donna
Barrett, Anthony G. M.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (43) : 14042 - 14043
[7] Biomimetic synthesis of (-)-longithorone A
Layton, ME
Morales, CA
Shair, MD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (05) : 773 - 775
[8] Enantioselective synthesis of (R)- and (S)-2-alkyl-1,4-butanediols via enantiomerically pure 3-alkyl-5-(menthyloxy)butyrolactones
Lee, N
Kim, YW
Chang, K
Kim, KH
Jew, SS
Kim, DK
[J]. TETRAHEDRON LETTERS, 1996, 37 (14) : 2429 - 2432
[9] Organic syntheses using indium-mediated and catalyzed reactions in aqueous media
Li, CJ
Chan, TH
[J]. TETRAHEDRON, 1999, 55 (37) : 11149 - 11176
[10] Structure elucidation of clavilactone D: an inhibitor of protein tyrosine kinases
Merlini, L
Nasini, G
Scaglioni, L
Cassinelli, G
Lanzi, C
[J]. PHYTOCHEMISTRY, 2000, 53 (08) : 1039 - 1041

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