Synthesis of novel C2-C3′-linked macrocyclic taxoids by means of highly regioselective Heck macrocyclization

被引：48

作者：

Geng, XD ^{[1
]}

Miller, ML ^{[1
]}

Lin, SN ^{[1
]}

Ojima, L ^{[1
]}

机构：

[1] SUNY Stony Brook, Dept Chem, Stony Brook, NY 11794 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 20期

关键词：

D O I：

10.1021/ol0354627

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel C2-C3'N-linked macrocyclic taxoids are synthesized using intramolecular Heck reaction in the key step. Macrocyclization proceeds with high regioselectivity in good yield. Taxoids bearing an olefin moiety at C2 and an iodide at C3'N give exo-products exclusively. However, the endo-products are formed with up to 100% regioselectivity just by switching the positions of the olefin and the iodide moieties. Some of these macrocyclic taxoids are significantly cytotoxic.

引用

页码：3733 / 3736

页数：4

共 37 条

[1] Synthesis of cyclic RGD derivatives via solid phase macrocyclization using the Heck reaction
Akaji, K
Teruya, K
Akaji, M
Aimoto, S
[J]. TETRAHEDRON, 2001, 57 (12) : 2293 - 2303
[2] [Anonymous], 1995, Taxol: Sci. Appl
[3] [Anonymous], 1999, ADV MED CH
[4] Conformationally restricted paclitaxel analogues: Macrocyclic mimics of the "hydrophobic collapse" conformation
Boge, TC
Wu, ZJ
Himes, RH
Vander Velde, DG
Georg, GI
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (20) : 3047 - 3052
[5] Crisp GT, 1998, CHEM SOC REV, V27, P427
[6] Palladium in action:: domino coupling and allylic substitution reactions for the efficient construction of complex organic molecules
de Meijere, A
Bräse, S
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) : 88 - 110
[7] de Meijere A, 1994, ANGEW CHEM, V106, P2473, DOI DOI 10.1002/ANGE.19941062307
[8] Synthesis of the benzophenone fragment of balanol via an intramolecular cyclization event
Denieul, MP
Laursen, B
Hazell, R
Skrydstrup, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) : 6052 - 6060
[9] LARGE RATE ACCELERATIONS IN THE STILLE REACTION WITH TRI-2-FURYLPHOSPHINE AND TRIPHENYLARSINE AS PALLADIUM LIGANDS - MECHANISTIC AND SYNTHETIC IMPLICATIONS
FARINA, V
KRISHNAN, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) : 9585 - 9595
[10] The intramolecular Heck reaction
Gibson, SE
Middleton, RJ
[J]. CONTEMPORARY ORGANIC SYNTHESIS, 1996, 3 (06): : 447 - 471

← 1 2 3 4 →