Isolation of Antipodal (-)-Versicolamide B and Notoamides L-N from a Marine-Derived Aspergillus sp.

被引：107

作者：

Tsukamoto, Sachiko ^{[1
,2
]}

Kawabata, Tetsuro ^{[1
]}

Kato, Hikaru ^{[1
]}

Greshock, Thomas J. ^{[3
]}

Hirota, Hiroshi ^{[4
]}

Ohta, Tornihisa ^{[1
]}

Williams, Robert M. ^{[3
,5
]}

机构：

[1] Chiba Univ, Grad Sch Sci, Inage Ku, Chiba 2638522, Japan

[2] Kanazawa Univ, Grad Sch Nat Sci & Technol, Kanazawa, Ishikawa 9201192, Japan

[3] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

[4] RIKEN Genom Sci Ctr, Tsurumi Ku, Yokohama, Kanagawa 230045, Japan

[5] Univ Colorado, Ctr Canc, Aurora, CO 80045 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 06期

关键词：

BIOMIMETIC TOTAL-SYNTHESIS; STEPHACIDIN-A; CONCISE; FUNGUS;

D O I：

10.1021/ol900071c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Antipodal (-)-versicolamide B and notoamides L-N were isolated from a marine-derived Aspergillus sp. The possible biosynthetic pathway of enantiomeric pairs of notoamide B and versicolamide B are proposed. Notoamide L is the first metabolite containing 25 carbons in the related prenylated indole alkaloids. Notoamide M is potentially a precursor to the proposed azadiene species involved in the putative intramolecular Diels-Alder reaction in the biogenesis of the bicyclo[2.2.2]diazaoctane ring system.

引用

收藏

页码：1297 / 1300

页数：4

相关论文

共 11 条

[1] Stereocontrolled total synthesis of (+)-paraherquamide B [J].

Cushing, TD ;

SanzCervera, JF ;

Williams, RM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (03) :557-579

[2] Isolation, structure elucidation, and biomimetic total synthesis of versicolamide B, and the isolation of antipodal (-)-stephacidin A and (+)-notoamide B from Aspergillus versicolor NRRL 35600 [J].

Greshock, Thomas J. ;

Grubbs, Alan W. ;

Jiao, Ping ;

Wicklow, Donald T. ;

Gloer, James B. ;

Williams, Robert M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (19) :3573-3577

[3] A concise, biomimetic total synthesis of stephacidin A and notoamide B [J].

Greshock, Thomas J. ;

Grubbs, Alan W. ;

Tsukamoto, Sachiko ;

Williams, Robert M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (13) :2262-2265

[4] A concise total synthesis of the notoamides C and D [J].

Grubbs, Alan W. ;

Artman, Gerald D., III ;

Tsukamoto, Sachiko ;

Williams, Robert M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (13) :2257-2261

[5] Notoamides A-D:: Prenylated indole alkaloids isolated from a marine-derived fungus, Aspergillus sp. [J].

Kato, Hikaru ;

Yoshida, Takushi ;

Tokue, Takanori ;

Nojiri, Yuka ;

Hirota, Hiroshi ;

Ohta, Tomihisa ;

Williams, Robert M. ;

Tsukamoto, Sachiko .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (13) :2254-2256

[6] Malbrancheamide, a new calmodulin inhibitor from the fungus Malbranchea aurantiaca [J].

Martínez-Luis, S ;

Rodríguez, R ;

Acevedo, L ;

González, MC ;

Lira-Rocha, A ;

Mata, R .

TETRAHEDRON, 2006, 62 (08) :1817-1822

[7] Stephacidin A and B: Two structurally novel, selective inhibitors of the testosterone-dependent prostate LNCaP cells [J].

Qian-Cutrone, JF ;

Huang, S ;

Shu, YZ ;

Vyas, D ;

Fairchild, C ;

Menendez, A ;

Krampitz, K ;

Dalterio, R ;

Klohr, SE ;

Gao, Q .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (49) :14556-14557

[8]

TSUKAMOTO S, J AM CHEM S IN PRESS

[9] Notoamides F-K, Prenylated Indole Alkaloids Isolated from a Marine-Derived Aspergillus sp. [J].

Tsukamoto, Sachiko ;

Kato, Hikaru ;

Samizo, Masayuki ;

Nojiri, Yuka ;

Onuki, Hiroyuki ;

Hirota, Hiroshi ;

Ohta, Tomihisa .

JOURNAL OF NATURAL PRODUCTS, 2008, 71 (12) :2064-2067

[10] REMARKABLE, ENANTIODIVERGENT BIOGENESIS OF BREVIANAMIDE-A AND BREVIANAMIDE-B [J].

WILLIAMS, RM ;

KWAST, E ;

COFFMAN, H ;

GLINKA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (08) :3064-3065