A comparative analysis of the total syntheses of the amphidinolide T natural products

被引:33
作者
Colby, EA [1 ]
Jamison, TF [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1039/b507315b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this article we compare and contrast the strategies and tactics used in the syntheses of the amphidinolide T family of natural products that have been reported by Furstner, Ghosh and ourselves. Similar approaches to the trisubstituted THF ring present in the targets are utilized in all of the syntheses, but each strategy showcases a different means of macrocyclization.
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页码:2675 / 2684
页数:10
相关论文
共 57 条
[31]   Absolute stereochemistry of amphidinolide C [J].
Kubota, T ;
Tsuda, M ;
Kobayashi, J .
ORGANIC LETTERS, 2001, 3 (09) :1363-1366
[32]  
Lam HW, 2002, ANGEW CHEM INT EDIT, V41, P508, DOI 10.1002/1521-3773(20020201)41:3<508::AID-ANIE508>3.0.CO
[33]  
2-7
[34]   A stereoelectronic model to explain the highly stereoselective reactions of nucleophiles with five-membered-ring oxocarbenium ions [J].
Larsen, CH ;
Ridgway, BH ;
Shaw, JT ;
Woerpel, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (51) :12208-12209
[35]   Total synthesis of amphidinolide X [J].
Lepage, O ;
Kattnig, E ;
Fürstner, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (49) :15970-15971
[36]   Total synthesis of proposed amphidinolide A via a highly selective ring-closing metathesis [J].
Maleczka, RE ;
Terrell, LR ;
Geng, F ;
Ward, JS .
ORGANIC LETTERS, 2002, 4 (17) :2841-2844
[37]   Catalytic asymmetric reductive coupling of alkynes and aldehydes:: Enantioselective synthesis of allylic alcohols and α-hydroxy ketones [J].
Miller, KM ;
Huang, WS ;
Jamison, TF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (12) :3442-3443
[38]   Nickel-catalyzed reductive coupling of alkynes and epoxides [J].
Molinaro, C ;
Jamison, TF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (27) :8076-8077
[39]   Nickel-catalyzed reductive cyclizations and couplings [J].
Montgomery, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (30) :3890-3908
[40]   SELECTIVE CARBON-CARBON BOND FORMATION VIA TRANSITION-METAL CATALYSIS .36. PALLADIUM-CATALYZED ACYLATION OF ORGANOZINCS AND OTHER ORGANOMETALLICS AS A CONVENIENT ROUTE TO KETONES [J].
NEGISHI, E ;
BAGHERI, V ;
CHATTERJEE, S ;
LUO, FT ;
MILLER, JA ;
STOLL, AT .
TETRAHEDRON LETTERS, 1983, 24 (47) :5181-5184