Total Synthesis of Seongsanamide B

被引：15

作者：

Shabani, Sadegh ^{[1
,2
]}

Hutton, Craig A. ^{[1
,2
]}

机构：

[1] Univ Melbourne, Sch Chem, Melbourne, Vic 3010, Australia

[2] Univ Melbourne, Bio21 Mol Sci & Biotechnol Inst, Melbourne, Vic 3010, Australia

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 11期

基金：

澳大利亚研究理事会;

关键词：

INTRAMOLECULAR O-ARYLATION; ENANTIOSELECTIVE SYNTHESIS; ISODITYROSINE; PEPTIDES; K-13; (S; S)-ISODITYROSINE; MACROLACTAMIZATION; MACROCYCLIZATION; DITYROSINE; OF4949-III;

D O I：

10.1021/acs.orglett.0c01642

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of the bicyclic depsipeptide natural product seongsanamide B is described. The successful approach employed solid-phase peptide synthesis of a core heptapeptide, incorporating on-resin esterification, followed by solutionphase macrolactamization and a late stage intramolecular Evans-Chan-Lam coupling to generate the biaryl ether of the isodityrosine unit.

引用

收藏

页码：4557 / 4561

页数：5

相关论文

共 44 条

[1] Entropically favorable macrolactamization. Synthesis of isodityrosine peptide analogues by tandem Erlenmeyer condensation-macrolactamization [J].

Bailey, KL ;

Molinski, TF .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2500-2504

[2] SYNTHESIS OF L,L-ISODITYROSINE [J].

BOGER, DL ;

YOHANNES, D .

TETRAHEDRON LETTERS, 1989, 30 (16) :2053-2056

[3] Synthesis of (9R,12S)- and (9S,12S)-cycloisodityrosine and their N-methyl derivatives [J].

Boger, DL ;

Zhou, JC ;

Borzilleri, RM ;

Nukui, S ;

Castle, SL .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) :2054-2069

[4] TOTAL SYNTHESIS OF L,L-ISODITYROSINE AND ISODITYROSINE-DERIVED AGENTS - K-13, OF4949-III, AND OF4949-IV [J].

BOGER, DL ;

YOHANNES, D .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (24) :6000-6017

[5] Total synthesis of an atropdiastereomer of RP-66453 and determination of its absolute configuration [J].

Bois-Choussy, M ;

Cristau, P ;

Zhu, JP .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (35) :4238-4241

[6] Total Synthesis of Ustiloxin D Utilizing an Ammonia-Ugi Reaction [J].

Brown, Aaron L. ;

Churches, Quentin I. ;

Hutton, Craig A. .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (20) :9831-9837

[7] Mild and nonracemizing conditions for Ullmann-type diaryl ether formation between aryl iodides and tyrosine derivatives [J].

Cai, Qian ;

He, Gang ;

Ma, Dawei .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (14) :5268-5273

[8] Future treatment for asthma [J].

Charriot, Jeremy ;

Vachier, Isabelle ;

Halimi, Laurence ;

Gamez, Anne-Sophie ;

Boissin, Clement ;

Salama, Marine ;

Cucu-Jarjour, Alina ;

Ahmed, Engi ;

Bourdin, Arnaud .

EUROPEAN RESPIRATORY REVIEW, 2016, 25 (139) :77-92

[9] Total Synthesis of Mycocyclosin [J].

Cochrane, James R. ;

White, Jonathan M. ;

Wille, Uta ;

Hutton, Craig A. .

ORGANIC LETTERS, 2012, 14 (09) :2402-2405

[10] The cyclization of peptides and depsipeptides [J].

Davies, JS .

JOURNAL OF PEPTIDE SCIENCE, 2003, 9 (08) :471-501

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