Synthesis of (±)-phthalascidin 650 analogue: new synthetic route to (±)-phthalascidin 622

被引：25

作者：

Razafindrabe, Christian R. ^{[1
,2
]}

Aubry, Sylvain ^{[1
]}

Bourdon, Benjamin ^{[1
]}

Andriantsiferana, Marta ^{[2
]}

Pellet-Rostaing, Stephane ^{[1
,3
]}

Lemaire, Marc ^{[1
]}

机构：

[1] CNRS, ICBMS, UMR5246, Lab Catalyse & Synth Organ, F-69622 Villeurbanne, France

[2] Univ Antananarivo, Lab Chim Prod Nat & Biotechnol LPNB, Antananarivo 101, Madagascar

[3] CNRS CEA UM2 ENSCM, ICSM, UMR 5257, Lab Tri Ion Syst Mol Autoassembles, F-30207 Bagnols Sur Ceze, France

来源：

TETRAHEDRON | 2010年 / 66卷 / 46期

关键词：

TETRAHYDROISOQUINOLINE ANTITUMOR ANTIBIOTICS; ECTEINASCIDIA-TURBINATA; PHTHALASCIDIN PT-650; CARIBBEAN TUNICATE; CYANOSAFRACIN B; ALKALOIDS; ET-743; AGENTS;

D O I：

10.1016/j.tet.2010.08.053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of functionalized phenolic alpha-amino-alcohol (+/-)-13 as synthetic precursor of the catechol tetrahydroisoquinoline structure of phthalascidin 650 is disclosed. Starting from 3-methylcatechol 5, eight steps of synthesis give rise to the synthesis of phenolic alpha-amino-alcohol (+/-)-13 in 27% overall yield. This synthetic strategy involves the elaboration of fully functionalized aromatic aldehyde 8 and its transformation into a phenolic alpha-amino-alcohol (+/-)-13, through a Knoevenagel condensation, simultaneous reduction of nitroketene and ester functions and hydrogenolysis of the benzyl protecting group. The pentacycle (+/-)-18 was obtained after four additional steps. The Pictet-Spengler cyclisation between the phenolic alpha-amino-alcohol (+/-)-13 and N-protected alpha-amino-aldehyde 4 allowed to obtain (1,3')-bis-tetrahydroisoquinoline 14 with N-methylated and N-Fmoc removed. The last step was a Swern oxidation for allowing an intramolecular condensation. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：9061 / 9066

页数：6

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